supporting information a flexible pinner preparation … supporting information a flexible pinner...
TRANSCRIPT
S1
Supporting Information
A flexible Pinner Preparation of Orthoesters. The model case of Trimethylorthobenzoate.
Marco Noè,* Alvise Perosa and Maurizio Selva*
Table of Contents:
S2 MS spectra for selected compounds
S7 1H NMR spectra of O-methyl-imidates 2a-c
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
S2
MS spectra for selected compounds
Figure S1. MS spectrum of O-methyl-propioimidate 2a.
Figure S2. MS spectrum of O-methyl-pentaneimidate 2b.
20 30 40 50 60 70 80 90 100 1100
100000
200000
300000
400000
500000
600000
700000
800000
m/z-->
AbundanceScan 482 (2.994 min): ORTOPR~1.D
25
28
33
41
44
52
56
58
6769
74 84
86
91
20 30 40 50 60 70 80 90 100 110 120 130 1400
200000
400000
600000
800000
1000000
1200000
1400000
1600000
1800000
2000000
m/z-->
AbundanceScan 245 (6.232 min): ORTOVAL.D
27
31
41
45
55
59
7174
8388 99
101
114115 127
130
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
S3
Figure S3. MS spectrum of O-methyl-benzoimidate 2c.
Figure S4. MS spectrum of trimethylorthopropionate 3a.
Figure S5. MS spectrum of trimethylorthopentanoate 3b.
30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 1800
50000
100000
150000
200000
250000
300000
350000
400000
450000
m/z-->
AbundanceScan 523 (9.401 min): MN460H2.D
44
50
5863
77
79
91
103
104
116121
134
139 154154 165
20 30 40 50 60 70 80 90 100 110 120 130 1400
500000
1000000
1500000
2000000
2500000
3000000
3500000
4000000
4500000
5000000
5500000
6000000
m/z-->
AbundanceScan 749 (4.607 min): MN574.D
26
29
39
4555
57
6972 78 88 97
103
106119 133
20 30 40 50 60 70 80 90 100 110 120 130 140 1500
200000
400000
600000
800000
1000000
1200000
1400000
1600000
1800000
m/z-->
AbundanceScan 409 (8.396 min): ORTOVAL.D
27
29
41
45
57
61
75 83
85
97
105
115117
131
132
147
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
S4
Figure S6. MS spectrum of trimethylorthobenzoate 3c.
Figure S7. MS spectrum of methyl-propionate 4a.
Figure S8. MS spectrum of methyl-pentanoate 4b.
20 40 60 80 100 120 140 160 180 200 2200
200000
400000
600000
800000
1000000
1200000
1400000
1600000
1800000
2000000
m/z-->
AbundanceScan 703 (12.227 min): ORTOBENZ.D
29
39
51
59
77
91
105
106119 136
151
167177187 199 213 227
10 20 30 40 50 60 70 80 90 100 110 1200
500000
1000000
1500000
2000000
2500000
3000000
3500000
4000000
m/z-->
AbundanceScan 205 (2.667 min): MN_ORTOP.D
21
29
334245
57
59
7073 79
88
93 101 110112 122
10 20 30 40 50 60 70 80 90 100 110 120 130 140 1500
200000
400000
600000
800000
1000000
1200000
1400000
1600000
m/z-->
AbundanceScan 117 (4.558 min): ORTOVAL.D
22
29
39
43
55
57
69
74
85
89 101 116 131
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
S5
Figure S9. MS spectrum of methylbenzoate 4c.
Figure S10. MS spectrum of benzamide 5c.
30 40 50 60 70 80 90 100 110 120 130 140 150 160 1700
500000
1000000
1500000
2000000
2500000
3000000
m/z-->
AbundanceScan 444 (8.449 min): MN460H2.D
43
51
52 6576
77
9293
105
114119 133
136
149154160 170
30 40 50 60 70 80 90 100 110 120 130 1400
100000
200000
300000
400000
500000
600000
700000
800000
900000
1000000
m/z-->
AbundanceScan 798 (12.713 min): MN460H2.D
44
50
54 63 74
77
86 92 99
105
108
121
122
134136 147
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
1H NNMR spectrra of methy
Figur
Figur
ylimidates 2
e S11. 1H NM
e S12. 1H NM
2a-c
MR of O-methy
MR of O-meth
yl-propioimid
yl-valeroimid
date 2a.
date 2b.
S6
6
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013