Water → HCID 11084479, compound

HRID 1806975Notes

Reaction equation

HRID 1806975 reaction equation
[CH3:1][C:2]1([CH2:6][OH:7])[CH2:5][O:4][CH2:3]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>ClCCl>[CH3:1][C:2]1([CH2:6][O:7][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:5][O:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 11084479HCID 11084479, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Step A To a solution of 3-methyl-3-oxetanemethanol (Aldrich) (3.5 g, 34 mmol) and triethylamine (10 g, 103 mmol) in dichloromethane (100 mL) at 0° C. was added a dichlormethane solution (20 mL) of methanesulfonyl chloride (Aldrich) (5.08 g, 45 mmol). The reaction mixture was stirred at 0° C. for 2 h. Water was added. Organic layer was separated, the aqueous layer was extracted with dichlormethane. The combined organic layers were washed with diluted aqueous HCl solution, saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated to give methanesulfonic acid 3-methyl-oxetan-3-ylmethyl ester as a yellow oil (6 g, 97%).

Workup

  1. customOrganic layer was separated
  2. extractionthe aqueous layer was extracted with dichlormethane
  3. washThe combined organic layers were washed with diluted aqueous HCl solution, saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-567c0b5109a946e7b04047af0160172c
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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