Water → 2-Cyclohexylethyl methylsulfonate

HRID 2190337Notes

Reaction equation

HRID 2190337 reaction equation
[CH:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[S:17](Cl)([CH3:20])(=[O:19])=[O:18].O>C(Cl)Cl.CCCCCCC.CCOC(C)=O>[CH:1]1([CH2:7][CH2:8][O:9][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 205082-CyclohexylethanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 227231732-Cyclohexylethyl methylsulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
0 °C

Procedure

150 mg (1.17 mmol, 1 eq) of 2-cyclohexylethanol were diluted in 4 mL of DCM, 214 μL (1.52 mmol, 1.3 eq) of triethylamine were added. The mixture was cooled to 0° C. and 100 μL (1.29 mmol, 1.1 eq) of mesyl chloride were added. The mixture was stirred for 15 min at 0° C. then water was added. The aqueous phase was extracted with dichloromethane. The organic phase was washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product (241 mg) was used directly for synthesis of 2. TLC: Rf: 0.48 (eluant: Heptane/EtOAc: 1/1).

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product (241 mg) was used directly for synthesis of 2

Sources & evidence

ORD record
ord-86bbd2f8e0374a14bd201b7543466671
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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