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

HRID 1416344ノート

反応式

HRID 1416344 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-294995fa0a754fc898750f6897e4d508
出典データセット
uspto-grants-1999_06
特許番号
US05912273

反応ノート

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