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

HRID 230810ノート

反応式

HRID 230810 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5c6023cf086e44689017b161735d6f20
出典データセット
uspto-grants-2009_07
特許番号
US07566803B2

反応ノート

読み込み中…