HCID 11163786, compound → HCID 86670673, compound

HRID 1754593Notes

Reaction equation

HRID 1754593 reaction equation
[CH2:1]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:10][C:9]=1[OH:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([O:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][C:48]=1[O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)/[CH:42]=[CH:43]/[CH2:44]O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[CH2:23]([O:22][C:11]1[CH:12]=[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:9]([OH:30])[C:10]=1[CH2:44]/[CH:43]=[CH:42]/[C:41]1[CH:46]=[CH:47][C:48]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[C:39]([O:38][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:40]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 11163786HCID 11163786, compoundHCID 69124070HCID 69124070, compound

Product 1

HCID 86670673HCID 86670673, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At rt under an N2 atmosphere, 25% H2SO4/SiO2 (1.6 g, 4 mmol) was added in one batch to the stirred mixture of 2-benzyl-3,5-bis(benzyloxy)phenol (3.96 g, 10 mmol) and (E)-3,4-bis(benzyloxy)cinnamyl alcohol (3.46 g, 10 mmol) in dry CH2Cl2 (80 mL). The resulting mixture was starred at rt overnight. After filtration and evaporation, the residue was purified by column chromatography on silica gel (EtOAc/n-hexane=1/7 v/v) and recrystallized from EtOAc and n-hexane to give a white solid, (3.4 g, 46.0% yield): mp 93-95° C.; 1H NMR (CDCl3, 400 MHz) δ 7.41-7.22 (m, 30H), 6.92 (s, 1H) 6.79 (s, 1H), 6.78 (d, J=4.0 Hz, 1H), 6.35 (A of AB, J=15.8 Hz, 1H), 6.26 (s, 1H), 6.13-6.07 (B of ABt, J=15.8, 5.0 Hz, 1H), 5.08 (s, 2H), 5.07 (s, 2H), 4.99 (s, 4H), 4.02 (s, 2H), 3.55 (d, J=5.0 Hz, 2H); 13C NMR (CDCl3, 400 MHz) δ 156.1, 155.6, 154.0, 148.9, 148.2, 141.1, 137.2, 137.1, 131.0, 130.1, 128.5, 128.4, 128.2, 127.8, 127.7, 127.6, 127.3, 127.2, 127.1, 126.5, 125.7, 119.7, 114.9, 112.4, 109.6, 107.3, 91.4, 71.1, 70.5, 70.3, 28.8, 26.6; HRMS (ESI): calcd for C50H44O5Na (M+Na) 747.3086, found 747.3096.

Workup

  1. filtrationAfter filtration and evaporation
  2. customthe residue was purified by column chromatography on silica gel (EtOAc/n-hexane=1/7 v/v)
  3. customrecrystallized from EtOAc and n-hexane
  4. customto give a white solid, (3.4 g, 46.0% yield)

Sources & evidence

ORD record
ord-3e71a68f12284e81990e07f47ebfec62
Source dataset
uspto-grants-2015_10
Patent number
US09169230B2

Reaction notes

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