Benzyl Alcohol → Benzyl cyclopropanesulfonate

HRID 2167723Notes

Reaction equation

HRID 2167723 reaction equation
[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1>C(Cl)Cl>[CH:1]1([S:4]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 2760919Cyclopropanesulfonyl chloride

Product 1

HCID 89618943Benzyl cyclopropanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Cyclopropyl sulfonyl chloride (2 g, 14.2 mmol) was added drop-wise at 0° C. to a solution of Benzyl alcohol (2.1 g, 28.4 mmol) and Pyridine (2.35 g, 29.8 mmol) in DCM (20 mL) and continued stirring at 25° C. for 16 h. The reaction mixture was diluted with DCM (100 mL), washed with 1N aq.HCl solution followed by water and brine; Organic layer collected was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the Benzyl cyclopropanesulfonate. 1H NMR (300 MHz, CD3OD) δ ppm 4.3-4.1 (2H, t), 2.7-2.6 (1H, m), 1.8-1.6 (2H, m), 1.6-1.4 (2H, m), 1.2-1.1 (4H, m), 1.0-0.9 (3H, t).

Workup

  1. washwashed with 1N aq
  2. customOrganic layer collected
  3. dry with materialwas dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8eb75a20b0142bfb6afe6b2e44a9803
Source dataset
uspto-grants-2015_06
Patent number
US09045478B2

Reaction notes

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