Toluene → (E)-3-biphenyl-4-yl-but-2-en-1-ol

HRID 984303

反応式

HRID 984303 の反応式
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)[CH:21]=[C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[CH3:23])C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CO>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24](/[C:22](/[CH3:23])=[CH:21]/[CH2:20][OH:19])=[CH:29][CH:28]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 545016723-(4-Biphenylyl)-2-butenoic acid ethyl ester

生成物 1

HCID 11264581(E)-3-biphenyl-4-yl-but-2-en-1-ol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A 1M solution of DIBAL-H in toluene (40 ml, 40 mmol) was added dropwise at −70° C. over 20 min. to a stirred solution of 3-biphenyl-4-yl-but-2-enoic acid ethyl ester (2.66 g, 10.0 mmol) in dry THF (100 ml) and the mixture stirred for 30 min. Methanol (2 ml) was added, followed by saturated aqueous Rochelle's salt (100 ml), and the resulting mixture extracted with ethyl acetate (200 ml), separated and the organic phase washed with brine, dried (Na2SO4), evaporated and dried in vacuo yielding (E)-3-biphenyl-4-yl-but-2-en-1-ol as colorless crystals: 1.94 g (86%)

後処理

  1. extractionthe resulting mixture extracted with ethyl acetate (200 ml)
  2. customseparated
  3. washthe organic phase washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-27295cf882084791ba5c76008a40c68f
出典データセット
uspto-grants-2005_03
特許番号
US06867218B2

関連ノート

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