Triethylamine → HCID 15008641, compound

HRID 654871Notes

Reaction equation

HRID 654871 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([CH2:26][OH:27])[CH:23]([CH3:24])[CH:22]([CH3:25])[O:21]2)=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2([CH2:26][O:27][S:2]([CH3:1])(=[O:4])=[O:3])[CH:23]([CH3:24])[CH:22]([CH3:25])[O:21]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15008640HCID 15008640, compound

Product 1

HCID 15008641HCID 15008641, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.13 ml (1.68 mmole) of methanesulfonyl chloride, followed by 0.24 ml (1.708 mmole) of triethylamine were added at 0° C. to a solution of 123 mg (0.543 mmole) of 2-(4-chlorophenyl)-3,4-dimethyl-2-hydroxymethyloxetane in 10 ml of methylene chloride, and the resulting mixture was stirred for 4 hours, during which time the reaction temperature was allowed to rise to room temperature. At the end of this time, a saturated aqueous solution of sodium hydrogencarbonate was added to the mixture, which was then extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel, eluted with a 10:1 by volume mixture of hexane and ethyl acetate, to afford 107 mg (yield 65%) of the title compound.

Workup

  1. customto rise to room temperature
  2. extractionwas then extracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. washeluted with a 10:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-2984bf1f988b470eb8fb21dba503ab4a
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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