3-Phenylprop-2-En-1-Ol → HCID 69314879, compound

HRID 1754591Notes

Reaction equation

HRID 1754591 reaction equation
[CH2:1](O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([OH:33])[CH:22]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:26]([O:25][C:23]1[CH:24]=[C:19]([O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:20]=[C:21]([OH:33])[C:22]=1[CH2:1]/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 3083-Phenylprop-2-En-1-OlHCID 118229213,5-dibenzyloxyphenol

Product 1

HCID 69314879HCID 69314879, compoundYield 62%

Procedure

Following the procedure in the literature (Li, L.; Chan, T. H. Org. Lett. 2001, 5, 739), cinnamyl alcohol was reacted with 3,5-dibenzyloxyphenol to yield (#a) as a white solid (62% yield); mp 76-78° C.; 1H NMR (CDCl3, 400 MHz) δ 7.40-7.24 (m, 15H), 6.48 (A of AB, J=15.9 Hz, 1H), 6.35 (B of ABt, J=15.9, 5.5 HZ, 1H), 6.27 (d, J=2.1 Hz, 1H), 6.16 (d, J=2.1 Hz, 1H), 5.07 (s, 1H), 5.02 (s, 2H), 4.99 (s, 2H), 3.59-3.57 (d, J=5.5 Hz, 2H); 13C NMR (CDCl3, 400 MHz) δ 158.5, 157.6, 155.4, 137.0, 136.8, 136.6, 130.2, 128.3, 128.2, 128.1, 128.0, 127.8, 127.6, 127.3, 127.0, 126.8, 125.8, 106.6, 94.8, 93.4, 70.1, 69.9, 26.2; HRMS (ESI) calcd for C29H26O3Na (M+Na) 445.1780, found 445.1793.

Sources & evidence

ORD record
ord-4d679364f52c4b77a961917af0bae2e0
Source dataset
uspto-grants-2015_10
Patent number
US09169230B2

Reaction notes

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