Methanesulfonyl chloride → HCID 87313767, compound

HRID 1628033Notes

Reaction equation

HRID 1628033 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH3:17])=[O:15]>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14127585HCID 14127585, compound

Product 1

HCID 87313767HCID 87313767, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (0.543 mL, 6.97 mmol) was added to a solution of methyl 2-(hydroxymethyl)cyclohexanecarboxylate (1.0 g, 5.8 mmol, Rieke) in DCM (4 mL) at about 0° C. TEA (0.971 mL, 6.97 mmol) was then added. The mixture was stirred at rt for about 4 h. The mixture was washed with water (10 mL) and extracted with EtOAc (2×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give (trans)-methyl 2-((methylsulfonyloxy)methyl)cyclohexanecarboxylate (1.4 g, 100%). LC/MS (Table 2, Method c) Rt=1.35 min; MS m/z 251 (M+H)+.

Workup

  1. washThe mixture was washed with water (10 mL)
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99f1f7e307a64d099a0ba4c5a77d4b45
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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