Triethylamine → (1-Cyanocyclopropyl)methyl methanesulfonate

HRID 1878332Notes

Reaction equation

HRID 1878332 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-33949fef109044149863d419b0c60cc4
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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