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

HRID 609581

反応式

HRID 609581 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 131721473(R)-2-butanol 4-bromobenzenesulfonate収率 67%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d5986d069af7448ea5744b080474cb62
出典データセット
uspto-grants-1999_12
特許番号
US05998413

関連ノート

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