Solketal → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate

HRID 79407Notes

Reaction equation

HRID 79407 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[CH3:10][S:11](Cl)(=[O:13])=[O:12].C(N(CC)CC)C>C(Cl)Cl>[CH3:10][S:11]([O:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 7528SolketalHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 15570840(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (400 mg, 3.03 mmol) in DCM (6 mL) at 0° C. was added methanesulfonyl chloride (381 mg, 3.33 mmol) and triethylamine (368 mg, 3.63 mmol. The cold bath was removed and the reaction mixture was stirred for 30 minutes. The mixture was diluted with DCM (5 mL). The organic phase was washed with water (4 mL) and brine (2 mL), and dried (Na2SO4). The solution was concentrated under reduced pressure to give the product (642 mg).

Workup

  1. customThe cold bath was removed
  2. additionThe mixture was diluted with DCM (5 mL)
  3. washThe organic phase was washed with water (4 mL) and brine (2 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6973e2a5d534758b3d1c9b5b6305e53
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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