Methanesulfonyl chloride → (2R,3R)-2-(2,3-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol

HRID 1936846ノート

反応式

HRID 1936846 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@:14]([OH:20])([C@H:17]([OH:19])[CH3:18])[CH2:15][OH:16].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@:14]([OH:20])([C@H:17]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:18])[CH2:15][O:16][S:2]([CH3:1])(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69944031(2R,3R)-2-(2,3-difluorophenyl)-1,2,3-butanetriol

生成物 1

HCID 86757716(2R,3R)-2-(2,3-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol収率 84%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

5.71 g (50 mmol) of methanesulfonyl chloride were added to a solution of 3.51 g (16.1 mmol) of (2R,3R)-2-(2,3-difluorophenyl)-1,2,3-butanetriol [obtained as described in Step 7(ii) above] in 18 ml of pyridine at 0° C. After stirring the resulting mixture for 0.5 hours, saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the product was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and then washed with aqueous sodium chloride solution and then concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel (100 g) column using a 1:1 mixture of ethyl acetate and hexane as the eluant to afford 5.04 g (yield 84%) of the title compound as a colorless oil.

後処理

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. washwashed with aqueous sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel (100 g) column
  6. additiona 1:1 mixture of ethyl acetate and hexane as the eluant

出典と根拠

ORDレコード
ord-012840c5261c43d4a6808b2e25df4f38
出典データセット
uspto-grants-2002_05
特許番号
US06391903B1

反応ノート

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