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

HRID 984303

반응식

HRID 984303 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-27295cf882084791ba5c76008a40c68f
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867218B2

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