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

HRID 2104373Notes

Reaction equation

HRID 2104373 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:17][C@H:16]1[CH2:18][O:19][CH2:13][C@H:14]1[O:15][S:9]([CH3:8])(=[O:11])=[O:10])(=[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 sequentially added dropwise to a solution of 1,4-anhydroerythritol (5.0 g) in methylene chloride (50 mL) under ice cooling, followed by stirring for 10 minutes under ice cooling. The reaction mixture was diluted with methylene chloride, and the diluted mixture was washed with 10% aqueous HCl, saturated aqueous sodium hydrogencarbonate, and saturated brine. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure, to thereby give the title compound (9.2 g).

Workup

  1. washthe diluted mixture was washed with 10% aqueous HCl, saturated aqueous sodium hydrogencarbonate, and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-2c86cbd01d0e42049dff611997f2095b
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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