Dichloromethane → (1-Cyanocyclopropyl)methyl methanesulfonate

HRID 342556Notes

Reaction equation

HRID 342556 reaction equation
[C:1]([C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1)#[N:2].C(N(CC)CC)C.C(Cl)Cl.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O>[CH3:18][S:19]([O:7][CH2:6][C:3]1([C:1]#[N:2])[CH2:5][CH2:4]1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 220282071-(Hydroxymethyl)cyclopropane-1-carbonitrile

Product 1

HCID 54220629(1-Cyanocyclopropyl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyanocycloprop-1-ylmethanol (4.31 g, 44.4 mmol), obtained as in the proceeding paragraph, triethylamine (9.04 mL, 64.8 mmol) and methylene chloride (78 mL) was cooled under argon to between 0° and 5° C. and methanesulfonyl chloride (4.67 mL, 59.9 mmol) was added slowly. The mixture was cooled 3 hours with stirring at 0° to 5° C., then diluted with water and extracted with methylene chloride. The extract was washed with 5% sodium bicarbonate, dried (MgSO4) and concentrated to dryness to give 1-cyano-cycloprop-1-ylmethyl methanesulfonate.

Workup

  1. temperaturewas cooled under argon to between 0° and 5° C.
  2. temperatureThe mixture was cooled 3 hours
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with 5% sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1b360edcb183493f80d7d91c931a7fdf
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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