Water → 2-Phenyl-1-propanol

HRID 1417806

반응식

HRID 1417806 반응식
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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 56980759(4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

생성물 1

HCID 142952-Phenyl-1-propanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-54957f7148bf443bb1dc3b27d1e40d92
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877317

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