Triethylamine → 1-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate

HRID 2109526Notes

Reaction equation

HRID 2109526 reaction equation
[CH:1]1([CH:4]([OH:16])[CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:16][CH:4]([CH:1]1[CH2:3][CH2:2]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 203899781-Cyclopropyl-3-(2-nitrophenyl)-propan-1-ol

Product 1

HCID 866212421-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.5 g of 1-cyclopropyl-3-(2-nitrophenyl)-propan-1-ol (2.26 mmol), 0.26 g of triethylamine (2.6 mmol) and 12 ml of dichloromethane is cooled to a temperature of 5° C. and 0.28 g of methanesulfonic acid chloride, dissolved in 3 ml of dichloromethane, is added dropwise. The resulting mixture is stirred for 16 hours at ambient temperature. The organic phase is washed with ice-water and dried over sodium sulfate and concentrated by evaporation. 1-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate is obtained in the form of a crude product, which is used directly in the cyclisation.

Workup

  1. additionis added dropwise
  2. washThe organic phase is washed with ice-water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4462d1eaab1543dab56f2fa0764df602
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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