Triethylamine → (1-Cyanocyclopropyl)methyl methanesulfonate

HRID 408859Notes

Reaction equation

HRID 408859 reaction equation
[OH:1][CH2:2][C:3]1([C:6]#[N:7])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl.C(=O)([O-])O.[Na+]>[CH3:15][S:16]([O:1][CH2:2][C:3]1([C:6]#[N:7])[CH2:5][CH2:4]1)(=[O:18])=[O:17]

Participants

6

Reactant 3

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

Product 1

HCID 54220629(1-Cyanocyclopropyl)methyl methanesulfonateYield 88.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A stirred mixture of 1-(hydroxymethyl)cyclopropanecarbonitrile (24.30 mmol, 2.36 g) in dichloromethane (30 mL) was treated with triethylamine (48.6 mmol, 6.83 mL, 4.92 g) and portionwise with methanesulfonyl chloride (31.6 mmol, 2.445 mL, 3.62 g) keeping the reaction mixture at 0° C. The solution was allowed to stir for 1 hour then diluted with saturated sodium hydrogencarbonate and extracted with 10% methanol/dichloromethane (×3). The organic layers were combined and concentrated under reduced pressure to give the intermediate (1-cyanocyclopropyl)methyl methanesulfonate (3.77 g).

Workup

  1. customat 0° C
  2. extractionextracted with 10% methanol/dichloromethane (×3)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1aee2912b6e42ba8fdfd6fadca482cb
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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