Ethyl-4-phenyl-3-furoate → (4-Phenylfuran-3-yl)methanol

HRID 273955

반응식

HRID 273955 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][O:14][CH:13]=1)=O)C>O1CCCC1>[C:17]1([C:16]2[C:12]([CH2:10][OH:9])=[CH:13][O:14][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 15037153Ethyl-4-phenyl-3-furoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 15037154(4-Phenylfuran-3-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

LiAlH4 (1.0M solution in hexane 1.14 ml, 1.14 mmol) was added dropwise to a solution of ethyl-4-phenyl-3-furoate (246 mg, assumed 1.28 mmol) in tetrahydrofuran (20 ml) at 0 degrees under argon. The solution was stirred and was allowed to warm to room temperature gradually over 1/2 hour. The mixture was quenched with saturated ammonium chloride and the organics were extracted into ethyl ether, and washed with H2O. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 20% ethyl acetate/hexanes. This was further purified by recrystallation (hexane/ethyl ether) to give the title compound as pale yellow crystals.

후처리

  1. customThe mixture was quenched with saturated ammonium chloride
  2. extractionthe organics were extracted into ethyl ether
  3. washwashed with H2O
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil, which
  7. customwas purified by flash chromatography on silica using 20% ethyl acetate/hexanes
  8. customThis was further purified by recrystallation (hexane/ethyl ether)

출처 및 근거

ORD 기록
ord-386df605fef84582903cae20aafa0cfd
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387606

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