Methanesulfonyl chloride → HCID 87344576, compound

HRID 1969392Notes

Reaction equation

HRID 1969392 reaction equation
[OH:1][CH2:2][C:3]1([OH:6])[CH2:5][CH2:4]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9]>C(Cl)Cl>[CH3:7][S:8]([O:1][CH2:2][C:3]1([O:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:5][CH2:4]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 158878901-(Hydroxymethyl)cyclopropan-1-ol

Product 1

HCID 87344576HCID 87344576, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a mixture of 1-(hydroxymethyl)cyclopropanol (100 mg, 1.14 mmol) and TEA (202 mg, 1.82 mmol, Shantou Xilong chemical factory) in 20 mL of dry CH2Cl2 under N2, was added MsCl (156 mg, 1.32 mmol, Shanghai Haiqu chemical Ltd.) dropwise via a syringe at −10° C. After stirring for 4 hrs at −10° C., the mixture was washed with ice-water and extracted with CH2Cl2 (30 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give the desired compound as pale yellow oil (139 mg, 50%).

Workup

  1. washthe mixture was washed with ice-water
  2. extractionextracted with CH2Cl2 (30 mL×3)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdc0bc69cc454848b7f35cfc155e731d
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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