Pyridine → (R)-2-butanol 4-bromobenzenesulfonate

HRID 609581

반응식

HRID 609581 반응식
[CH3:1][C@@H:2]([OH:5])[CH2:3][CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.N1C=CC=CC=1.ClCCl>CN(C)C1C=CN=CC=1.O>[CH3:1][C@@H:2]([OH:5])[CH2:3][CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:15])(=[O:5])=[O:14])=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7396p-Bromobenzenesulfonyl chlorideHCID 84682(-)-2-Butanol

생성물 1

HCID 131721473(R)-2-butanol 4-bromobenzenesulfonate수율 67%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매

실험 절차

A mixture of 8.2 g of (R)-(-)2-butanol, 31.5 g of 1-bromo-4-benzenesulfonyl chloride, 1.0 g of N,N-dimethyl-4-pyridinamine, 55.5 ml of pyridine and 293 ml of dichloromethane was stirred for 3 days at room temperature. After the addition of water, stirring was continued for 1 hour. The reaction mixture was washed twice with a diluted hydrochloric acid solution and once with water, dried, filtered and evaporated in vacuo. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 11.5 g (35.6%) of (R)-2-butanol 4-bromobenzenesulfonate (ester) (interm. 3).

후처리

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. washThe reaction mixture was washed twice with a diluted hydrochloric acid solution and once with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography over silica gel
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

출처 및 근거

ORD 기록
ord-d5986d069af7448ea5744b080474cb62
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998413

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