Water → Cycloheptylmethyl methanesulfonate

HRID 1739740Notes

Reaction equation

HRID 1739740 reaction equation
[CH:1]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>ClCCl>[CH3:17][S:18]([O:9][CH2:8][CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 78193Cycloheptanemethanol

Product 1

HCID 21866479Cycloheptylmethyl methanesulfonateYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cycloheptylmethanol (1.0 g, 7.81 mmol) in dichloromethane (20 ml) at 0° C. under nitrogen was added triethylamine (1.63 ml, 1.5 mol. equiv.) Methanesulphonyl chloride (0.73 ml, 1.2 mol. equiv.) was added, dropwise, and the reaction allowed to stir for two hours at room temperature. Water (50 ml) and dichloromethane (50 ml) were added. The organic phase was separated, washed with water (2×50 ml) and then dried over anhydrous magnesium sulphate. The solution was then filtered and the solvent removed under reduced pressure to give the title compound as an oil (1.66 g).

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with water (2×50 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationThe solution was then filtered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-80caafe921d74b35bf3c6b05b6cddaf8
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

Loading…