Water → HCID 54074590, compound

HRID 1680998Notes

Reaction equation

HRID 1680998 reaction equation
[CH2:1]([O:5][C@H:6]([CH3:10])[C@H:7]([OH:9])[CH3:8])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>ClCCl>[CH3:18][S:19]([O:9][C@@H:7]([C@H:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH3:10])[CH3:8])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15065685HCID 15065685, compound

Product 1

HCID 54074590HCID 54074590, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g of (2R,3R)-3-butoxy-2-butanol and 0.83 g of triethylamine were dissolved in 10 ml of dichloromethane. Thereto was dropwise added 0.94 g of methanesulfonyl chloride with ice-cooling. The mixture was stirred overnight at room temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with dilute hydrochloric acid and an aqueous sodium bicarbonate solution in this order, and then dried and concentrated under reduced pressure. The residue was subjected to Kugel-rohr distillation (1 mmHg) to obtain 1.30 g of (2R,3R)-3-butoxy-2-butyl methanesulfonate.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with dilute hydrochloric acid
  4. dry with materialan aqueous sodium bicarbonate solution in this order, and then dried
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was subjected to Kugel-rohr distillation (1 mmHg)

Sources & evidence

ORD record
ord-bcc32e46f37e48d19423c1704a615f25
Source dataset
uspto-grants-1992_12
Patent number
US05167863

Reaction notes

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