Triethylamine → HCID 10539266, compound

HRID 657630Notes

Reaction equation

HRID 657630 reaction equation
[CH3:1][C@@H:2]([OH:7])[CH2:3][C@H:4]([OH:6])[CH3:5].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:6][C@@H:4]([CH2:3][C@H:2]([O:7][S:16]([CH3:15])(=[O:18])=[O:17])[CH3:1])[CH3:5])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27236832,4-Pentanediol, (-)-

Product 1

HCID 10539266HCID 10539266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R,4R)-2,4-pentanediol (15.0 g), triethylamine (45.2 mL) and dichloromethane (350 mL) is cooled at a temperature close to 0° C. Methanesulfonyl chloride (24.5 mL) is added dropwise. The mixture is stirred for 3 h at a temperature close to 0° C., hydrolysed with a 1.5 N aqueous hydrochloric solution (100 mL) and extracted with dichloromethane. The organic extracts are pooled, washed with a saturated aqueous solution of sodium hydrogenocarbonate, then a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure to give 36.06 g of (2R,4R)-2,4-pentanediol dimethanesulfonate as a brown oil used without further purification.

Workup

  1. customclose to 0° C
  2. extractionextracted with dichloromethane
  3. washwashed with a saturated aqueous solution of sodium hydrogenocarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0be70acd809d4b5ba3d8c6c4b317fbab
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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