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

HRID 1392750Notes

Reaction equation

HRID 1392750 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-d522cae348de43efb0c36ae4accdf1c5
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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