Methanesulfonyl chloride → HCID 58557176, compound

HRID 1969542Notes

Reaction equation

HRID 1969542 reaction equation
[CH2:1]([CH:3]1[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][CH:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:2].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH2:1]([CH:3]1[CH2:7][CH:6]([CH2:8][O:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:5][CH:4]1[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58557598HCID 58557598, compound

Product 1

HCID 58557176HCID 58557176, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylate (0.220 g, 0.964 mmol) in DCM (5 mL) was added TEA (0.16 mL, 1.15 mmol) and methanesulfonyl chloride (0.083 mL, 1.06 mmol) at about 0° C. The reaction mixture was allowed to warm to about 25° C. and stirred at about 25° C. for about 16 h. The reaction mixture was partitioned between water (20 mL) and DCM (20 mL). The aqueous solution was washed with DCM (2×20 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give tert-butyl 2-ethyl-4-((methylsulfonyloxy)methyl)cyclopentanecarboxylate (0.295 g, 100%): LC/MS (Table 1, Method b) Rt=2.55 min; MS m/z: 307 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water (20 mL) and DCM (20 mL)
  2. washThe aqueous solution was washed with DCM (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9d39f83b89d547429bbd5bddcd692722
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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