Methanesulfonyl chloride → (2R,3R)-2-(2,5-difluorophenyl)-1,3-bis(methanesulfonyl)-2-butanol

HRID 1937156Notes

Reaction equation

HRID 1937156 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@:9]([OH:15])([C@H:12](O)[CH3:13])[CH2:10]O.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@:9]([OH:15])([C@H:12]([S:17]([CH3:16])(=[O:19])=[O:18])[CH3:13])[CH2:10][S:17]([CH3:16])(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69943979(2R,3R)-2-(2,5-difluorophenyl)-1,2,3-butanetriol

Product 1

HCID 69942689(2R,3R)-2-(2,5-difluorophenyl)-1,3-bis(methanesulfonyl)-2-butanolYield 218.6%

Procedure

In the same manner as that described in Example 7(iii) above, 4.80 g (10.1 mmol) of (2R,3 R)-2-(2,5-difluorophenyl)-1,2,3-butanetriol [prepared as described in Step 8(ii) above] were reacted with 7.75 g (67.8 mmol) of methanesulfonyl chloride and the resulting product was purified by chromatography on a silica gel (110 g) column using a 1:2 to 1:1 mixture of ethyl acetate and hexane as the eluant to afford 7.56 g (yield 92%) of the title compound as a colorless oil.

Workup

  1. customthe resulting product was purified by chromatography on a silica gel (110 g) column
  2. additionto 1:1 mixture of ethyl acetate and hexane as the eluant

Sources & evidence

ORD record
ord-c5ee84158c0b43f483ef2227331eb89c
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

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