Water → 2-Phenyl-1-propanol

HRID 368825

反応式

HRID 368825 の反応式
C1(C[C@H]2COC(=O)N2[C:14](=[O:23])[CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:17]1([CH:15]([CH3:16])[CH2:14][OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 56980759(4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

生成物 1

HCID 142952-Phenyl-1-propanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone (XLI, Isomer I, 2.651 g, 8.57 mmol) in THF (10 ml) is added dropwise to a cooled slurry of lithium aluminum hydride (0.3518 g, 9.27 mmol) in THF (10 ml). After the mixture had stirred for 28 min at 0°, water (0.35 ml) is added and the mixture is stirred for 15 min. Sodium hydroxide (15% aqueous solution, 0.35 ml) is added and again the mixture is allowed to stir for 15 min. After the final addition of water (1.05 ml), the salts are removed by filtration and washed with ether. The combined filtrates are washed with saline, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (15/85). The appropriate fractions are pooled and concentrated to give 2-phenylpropanol (XLIII, Isomer Ia), NMR (CDCl3) 1.28, 1.35, 2.95, 3.71 and 7.26 δ.

後処理

  1. stirringthe mixture is stirred for 15 min
  2. stirringto stir for 15 min
  3. customthe salts are removed by filtration
  4. washwashed with ether
  5. washThe combined filtrates are washed with saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel eluting with ethyl acetate/hexane (15/85)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-06a1b8bfc70b4a6ba409fc0cef7a3db4
出典データセット
uspto-grants-2000_10
特許番号
US06133446

関連ノート

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