Phosphate → cis-Stilbene
Reaction equation
P([O-])([O-])([O-])=O.I[C:7]1[CH:8]=[C:9](/[CH:17]=[CH:18]\[C:19]2[CH:24]=[CH:23][C:22](OC)=[C:21](O)[CH:20]=2)[CH:10]=[C:11](OC)[C:12]=1OC>>[C:9]1(/[CH:17]=[CH:18]\[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:10]=[CH:11][CH:12]=[CH:7][CH:8]=1Participants
Procedure
The phosphorylation reaction used to obtain phosphate 15 was repeated with Z-stilbene 14a (2.39 g, 0.95 mmol) to obtain 0.55 g of Z-stilbene 17 in 86% yield as a colorless oil. b.p. dec. 274° C. (0.01 mmHg); HRMS calc for C31H31PO7 [M+H]+ 673.0852; found [+H]+, 673.0808. 1H-NMR (300 MHz, CDCl3) δ 3.51 (s, 3H), 3.65 (s, 3H), 3.72 (s, 3H), 5.04 (s, 2H), 5.06 (s, 2H), 6.36 (d, 1H, J=9 Hz), 6.42 (d, 1H, =9 Hz), 6.77 (d, 1H, J=1.2 Hz), 6.89 (d, 1H, J=6 Hz), 7.02 (d, 1H, J=6 Hz), 7.01 (s, 1H), 7.19 (d, 1H, J=1.2 Hz), 7.28 (m, 10H); and 13C-NMR (75 MHz, CDCl3) δ 56.20, 56.50, 60.73, 71.18, 71.24, 92.73, 113.72, 114.23, 122.58, 122.61, 128.10, 128.93, 129.50, 129.56, 130.18, 130.85, 130.86, 131.87, 136.26, 136.66, 136.73, 140.32, 140.3, 149.12, 151.21, 151.25, 153.26.
Workup
- customThe phosphorylation reaction
Sources & evidence
- ORD record
- ord-4dbfafa834ae45bdaf45b5ea88d5ea51
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507851B2
Reaction notes
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