3,4-Dimethoxybenzophenone → 1-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene

HRID 1385440Notes

Reaction equation

HRID 1385440 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[CH:22]=[CH:21][C:20](OC)=[C:19](OC)[CH:18]=2)=[CH:12][C:13](OC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(C=CC=1OC)C(C1C=CC=CC=1)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 2867423,4-DimethoxybenzophenoneHCID 2733832Lithium HexamethyldisilazideHCID 9820154Methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate

Product 1

HCID 541210301-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

1-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene was prepared analogously to methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate using 3,4-dimethoxybenzophenone (3 g, 12.4 mmol), (ethyl)triphenylphosphonium bromide (5.1 g, 13.6 mmol) and lithium hexamethyldisilazide (13.6 mL, 13.6 mmol, 1M) with a reaction time of 4 hours at room temperature. The crude mixture was purified by flash column chromatography (silica gel, 10% hexane/methylene chloride) to afford 1.3 g (41%) of a mixture of the E and Z isomers as a white solid: mp 72-73° C.; 1H NMR (CDCl3) δ7.40-6.80 (m, 16 H), 6.16-6.08 (m, 2 H), 3.90-3.80 (m, 12 H), 1.97-1.73 (m, 6 H); 13C NMR (CDCl3) δ148.6, 148.5, 148.1, 147.8, 142.9, 142.3, 142.0, 140.0, 136.0, 132.5, 129.9, 128.0, 128.0, 127.1, 126.7, 126.6, 123.8, 122.6, 122.5, 119.8, 113.6, 110.8, 110.7, 110.4, 55.8, 55.8, 55.7, 15.7, 15.5; Anal. Calcd for C17H18O2. Theoretical: C, 80.28; H, 7.13. Found: C, 79.94; H, 7.12.

Workup

  1. customwith a reaction time of 4 hours
  2. customat room temperature
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 10% hexane/methylene chloride)

Sources & evidence

ORD record
ord-22df79d5779e424e940dd3f8970771ba
Source dataset
uspto-grants-2001_07
Patent number
US06262101B1

Reaction notes

Loading…