Triethylamine → (3R,4S)-4-[(Methylsulfonyl)oxy]tetrahydro-3-furanyl methanesulfonate

HRID 902857Notes

Reaction equation

HRID 902857 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]1[O:19][CH2:18][C@@H:16]([OH:17])[C@H:14]1[OH:15]>C(Cl)Cl>[CH3:8][S:9]([O:15][C@H:14]1[C@@H:16]([O:17][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:18][O:19][CH2:13]1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6417731,4-Anhydroerythritol

Product 1

HCID 57931119(3R,4S)-4-[(Methylsulfonyl)oxy]tetrahydro-3-furanyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (12.0 ml) and methanesulfonyl chloride (3.6 ml) were successively added dropwise to a solution of 1,4-anhydroerythritol (5.0 g) in methylene chloride (50 ml) under ice cooling, and the mixture was stirred for 10 minutes under ice cooling. The reaction mixture was diluted with methylene chloride and washed with 10% hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride. After the resultant organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (9.2 g).

Workup

  1. washwashed with 10% hydrochloric acid
  2. dry with materialAfter the resultant organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6d39f559f2764ea9bb2cdbcc0136c4cb
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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