Phenol → (2R)-2-(Phenoxymethyl)oxirane

HRID 20375

반응식

HRID 20375 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:10]1[CH2:12][C@@H:11]1[CH2:13]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O>CN(C)C=O>[O:7]([CH2:13][C@H:11]1[CH2:12][O:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester

생성물 1

HCID 1534344(2R)-2-(Phenoxymethyl)oxirane수율 81.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Add phenol (1.089 g, 11.572 mmol) to a slurry of sodium hydride (0.347 g, 14.465 mmol) in N,N-dimethylformamide (77.1 mL) and stir at room temperature for 40 minutes. Add 3-nitrobenzenesulfonic acid (R)-1-oxiranylmethyl ester (3.00 g, 11.572 mmol) and stir at room temperature for 16 hours (J. Org. Chem., 54, 1296-1304 (1989). Quench with saturated aqueous ammonium chloride (75 mL), dilute with water (75 mL) and extract with diethyl ether (3×300 mL). Combine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL), dry (magnesium sulfate), filter and purify (silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes) to give the desired compound as a clear liquid (1.410 g, 81.1%).

후처리

  1. customQuench with saturated aqueous ammonium chloride (75 mL)
  2. additiondilute with water (75 mL)
  3. extractionextract with diethyl ether (3×300 mL)
  4. washCombine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL)
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. custompurify
  8. wash(silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-dcce78decbd644babd0ddb737e71f34b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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