Methanesulfonyl chloride → HCID 10878028, compound

HRID 520356Notes

Reaction equation

HRID 520356 reaction equation
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](=[O:6])[CH3:5].CCN(C(C)C)C(C)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.CCOC(C)=O>[CH3:18][S:19]([O:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](=[O:6])[CH3:5])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 111943184-Hydroxy-3,3-dimethylbutan-2-one

Product 1

HCID 10878028HCID 10878028, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-3,3-dimethylbutan-2-one (9.7 g, 84 mmol) and DIPEA (16.04 mL, 92 mmol) in DCM (50 mL) cooled to 0° C. was dropwise added methanesulfonyl chloride (7.16 mL, 92 mmol). The reaction mixture was stirred at rt for 18 h. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3, sat. NaCl, dried (MgSO4), filtered and concentrated to yield 2,2-dimethyl-3-oxobutyl methanesulfonate (14.6 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.21 (2H, s), 3.04 (3H, s), 2.21 (3H, s), 1.25 (6H, s).

Workup

  1. washwashed with sat. NaHCO3, sat. NaCl
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d17fcd7e698f4a4f8f7702d0a7f62172
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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