Methanesulfonyl chloride → HCID 22346726, compound

HRID 432229Notes

Reaction equation

HRID 432229 reaction equation
[CH:1](=[C:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)[CH2:2][CH3:3].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>N1C=CC=CC=1>[CH3:9][S:10]([O:8][CH:6]1[CH2:7][C:4](=[CH:1][CH2:2][CH3:3])[CH2:5]1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15272330HCID 15272330, compound

Product 1

HCID 22346726HCID 22346726, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-propylidene-1-cyclobutanol (0.344 g, 0.00307 mol) in pyridine (5 mL) was cooled to 0° C. Methanesulfonyl chloride (0.422 g, 0.00369 mol) was added dropwise, keeping the temperature below 2° C. The mixture was stirred for two hours, and then poured into ice water (15 mL) and extracted with ethyl ether (2×10 mL). The combined organic layers were washed with water (3×10 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give 3-propylidenecyclobutyl methanesulfonate (0.492 g, 0.00221 mol) as a yellow oil.

Workup

  1. customthe temperature below 2° C
  2. extractionextracted with ethyl ether (2×10 mL)
  3. washThe combined organic layers were washed with water (3×10 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e711d40093ac4cf1a06859d95c8f86c1
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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