Aluminium lithium hydride → [4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylphenyl]methanol

HRID 230810노트

반응식

HRID 230810 반응식
[Si:1]([O:8][CH:9]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:32]=[CH:31][C:26]([C:27](OC)=[O:28])=[C:25]([CH3:33])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Si:1]([O:8][CH:9]([C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:32]=[CH:31][C:26]([CH2:27][OH:28])=[C:25]([CH3:33])[CH:24]=2)([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:14][C:13]=1[CH3:34])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 57763479Methyl 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methyl-benzoate

생성물 1

HCID 57763514[4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylphenyl]methanol수율 99.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 0° C. solution of the methyl 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methyl-benzoate (4.37 g, 8.09 mmol) in THF (50 mL) is added LiAlH4 (0.31 g, 8.09 mmol). The reaction is stirred for 10 m and allowed to warm to RT overnight. The mixture is cooled to 0° C. and quenched successively with H2O (0.3 mL), 15% NaOH (0.3 mL) and H2O (0.9 mL). The mixture is stirred for 10 m, warmed to RT, stirred for 20 m, filtered through celite with EtOAc (100 mL) wash, and concentrated to give the title compound (4.14 g, 8.08 mmol, 99%).

후처리

  1. temperatureThe mixture is cooled to 0° C.
  2. customquenched successively with H2O (0.3 mL), 15% NaOH (0.3 mL) and H2O (0.9 mL)
  3. stirringThe mixture is stirred for 10 m
  4. temperaturewarmed to RT
  5. stirringstirred for 20 m
  6. filtrationfiltered through celite with EtOAc (100 mL)
  7. washwash
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5c6023cf086e44689017b161735d6f20
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566803B2

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