3-Phenyl-2-triethylsilyl-4furaldehyde → 3-Phenyl-2-triethylsilyl-4-furanmethanol

HRID 273963

반응식

HRID 273963 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2[C:17]([CH:18]=[O:19])=[CH:16][O:15][C:14]=2[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[C:7]1([C:13]2[C:17]([CH2:18][OH:19])=[CH:16][O:15][C:14]=2[Si:20]([CH2:23][CH3:24])([CH2:25][CH3:26])[CH2:21][CH3:22])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

4

반응물 2

HCID 150371493-Phenyl-2-triethylsilyl-4furaldehydeHCID 21226445Aluminium lithium hydride

생성물 1

HCID 150371503-Phenyl-2-triethylsilyl-4-furanmethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

LiAlH4 (1.0M solution in hexane, 1.48 ml, 1.48 mmol) was added dropwise to a solution of 3-phenyl-2-triethylsilyl-4-furaldehyde (422 mg, 1.48 mmol) in tetrahydrofuran (10 ml) at 0 degrees under argon. This mixture was warmed to room temperature, quenched with ice-cold 5% (V/V) hydrochloric acid and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, H2O and brine. The dried extracts (magnesium sulfate) were concentrated to an oil which was purified by flash chromatography on silica using 20% ethyl acetate/hexanes to give the title compound. IR (neat): 3300 (broad); 2953 cm-1.

후처리

  1. customquenched with ice-cold 5% (V/V) hydrochloric acid
  2. extractionthe organics were extracted into ethyl ether
  3. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
  4. concentrationThe dried extracts (magnesium sulfate) were concentrated to an oil which
  5. customwas purified by flash chromatography on silica using 20% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-967822ffd5dd4100847391fbab454d57
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387606

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