Dimethylformamide → Z-4-[4-(2-benzyloxyethoxy)-phenyl]-4-(4-benzyloxyphenyl)-3-phenyl-but-3-en-1-ol

HRID 1416344Notes

Reaction equation

HRID 1416344 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:25][OH:26])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:40]([O:47][CH2:48][CH2:49]Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>[Cl-].[Na+].O>[CH2:40]([O:47][CH2:48][CH2:49][O:39][C:36]1[CH:37]=[CH:38][C:33](/[C:22](/[C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:17][CH:18]=2)=[C:23](\[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)/[CH2:24][CH2:25][OH:26])=[CH:34][CH:35]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 540271694-[1-(4-Benzyloxyphenyl)-4-hydroxy-2-phenyl-but-1-enyl]phenol

Product 1

HCID 67566056Z-4-[4-(2-benzyloxyethoxy)-phenyl]-4-(4-benzyloxyphenyl)-3-phenyl-but-3-en-1-ol

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The reaction vessel was charged with sodium hydride (0.43 g, 0.0178 mol) and dimethyl formamide (34 ml). 4-[1-(4-Benzyloxyphenyl)-4-hydroxy-2-phenyl-but-1-enyl]phenol (5 g, 0.0118 mol) prepared by the method of U.S. Pat. No. 4,996,225 was dissolved to dimethyl formamide (6 ml), added to the mixture at room temperature and stirring was continued for half an hour. Then benzyl-(2-bromoethyl)ether (3.06 g, 0.014 mol) was added dropwise during 20 minutes to the reaction mixture and stirring was continued for additional 4 hours. The reaction mixture was poured into brine and extracted with ethyl acetate. Organic layer was washed with 2 N hydrogen chloride solution and twice with water, dried and evaporated to dryness. The product was purified by flash chromatography (toluene: methanol, 9.8:0.2). Yield 2.8 g.

Workup

  1. additionadded to the mixture at room temperature
  2. waitwas continued for half an hour
  3. stirringstirring
  4. extractionextracted with ethyl acetate
  5. washOrganic layer was washed with 2 N hydrogen chloride solution and twice with water
  6. customdried
  7. customevaporated to dryness
  8. customThe product was purified by flash chromatography (toluene: methanol, 9.8:0.2)

Sources & evidence

ORD record
ord-294995fa0a754fc898750f6897e4d508
Source dataset
uspto-grants-1999_06
Patent number
US05912273

Reaction notes

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