Diisobutylaluminumhydride → (3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol

HRID 502372

반응식

HRID 502372 반응식
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)=[C:7]([O:19][CH2:20][CH3:21])[CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]=1[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18]1)[CH3:21]

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 669121583,5-Diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester

생성물 1

HCID 66912179(3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol수율 100%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 3,5-diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester (1.51 g, 4.98 mmol) in toluene (5 mL) was added slowly over a time period of 15 min under slight cooling to 20° C. a solution of diisobutylaluminium hydride (8.9 mL, 12.45 mmol, 20% solution in toluene). After 1 h, the excess hydride was quenched by cautious addition of water (10 mL) and a 28% solution of sodium hydoxide (2 mL). The mixture was stirred for 30 min and the organic phase filtered over Hyflo. The aqueous layer was extracted with toluene (2×50 mL), the combined organic phases washed with a sat. solution of sodium chloride (2×50 mL) and concentrated by evaporation under reduced pressure to afford 1.30 g (100%) of (3,5-diethoxy-4-pyrrol-1-yl-phenyl)-methanol. The crude alcohol (1.30 g, 4.98 mmol, 1.0 equiv) was dissolved in toluene (20 mL) and MnO2 (7.79 g, 89.5 mmol, 18.0 equiv) was added. The reaction mixture was heated to reflux for 7 h, after which time the reaction was filtered through Hyflo and concentrated yielding 1.15 g (89% yield) of the title compound.

후처리

  1. customthe excess hydride was quenched by cautious addition of water (10 mL)
  2. filtrationthe organic phase filtered over Hyflo
  3. extractionThe aqueous layer was extracted with toluene (2×50 mL)
  4. washthe combined organic phases washed with a sat. solution of sodium chloride (2×50 mL)
  5. concentrationconcentrated by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-5dc572e3304648388b9b5c1bc66aff34
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772253B2

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