Methanesulfonyl chloride → HCID 72574159, compound

HRID 271385Notes

Reaction equation

HRID 271385 reaction equation
[Si:1]([O:8][CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH:13]1[F:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:26][S:27]([O:18][CH:15]1[CH2:16][CH2:17][CH:12]([O:11][CH2:10][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]([F:19])[CH2:14]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69275924HCID 69275924, compound

Product 1

HCID 72574159HCID 72574159, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexanol (8.46 g, 22.9 mmol) in dichloromethane (100 mL) at 0° C. was added methanesulfonyl chloride (2.49 mL, 32.1 mmol) and diisopropylethylamine (11.1 mL, 64.1 mmol). The reaction mixture was stirred for 1 min, diluted with dichloromethane and washed with 5% potassium bisulfate. The layers were separated and the aqueous extracted with dichloromethane (3×). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (hexane: ethyl acetate 70:30) gave 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexyl methanesulfonate (9.77 g, 100% yield) as a clear oil.

Workup

  1. washwashed with 5% potassium bisulfate
  2. customThe layers were separated
  3. extractionthe aqueous extracted with dichloromethane (3×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (hexane: ethyl acetate 70:30)

Sources & evidence

ORD record
ord-dd4d3f494d9d4d96b53d35a2665d636f
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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