Methanesulfonyl chloride → HCID 22347150, compound

HRID 897654Notes

Reaction equation

HRID 897654 reaction equation
[OH:1][CH:2]1[CH2:5][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([O:1][CH:2]1[CH2:5][C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:3]1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14728564Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

Product 1

HCID 22347150HCID 22347150, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of diethyl 3-hydroxy-1,1-cyclobutanedicarboxylate (0.268 g, 0.00116 mol) in pyridine (7 mL) was cooled to 0° C. Methanesulfonyl chloride (0.11 mL, 0.160 g, 0.00140 mol) was added dropwise, keeping the temperature below 2° C. The mixture was stirred for four hours, and then poured into ice water (20 mL) and extracted with ethyl ether (2×10 mL). The combined organic layers were washed with water (3×10 mL) and brine (10 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give diethyl 3-[(methylsulfonyl)oxy]-1,1-cyclobutanedicarboxylate (0.302 g, 0.00102 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) and brine (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-66a74730dd0643f88187b722e1c30978
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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