Triethylamine → 2-[3-(Benzenesulfonyl)-1,1,1-trifluoropropan-2-yl]-2-methyloxirane

HRID 728353Notes

Reaction equation

HRID 728353 reaction equation
CS(Cl)(=O)=O.[CH3:6][C:7]([OH:25])([CH:10]([C:21]([F:24])([F:23])[F:22])[CH2:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:8]O.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:6][C:7]1([CH:10]([C:21]([F:22])([F:23])[F:24])[CH2:11][S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:14])[O:25][CH2:8]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13988926HCID 13988926, compound

Product 1

HCID 147728592-[3-(Benzenesulfonyl)-1,1,1-trifluoropropan-2-yl]-2-methyloxiraneYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, 1.45 ml (18.7 mmoles) of methanesulfonyl chloride was added under ice cooling to a solution of 3.90 g (12.5 mmoles) of the compound (18) and 6.10 ml (43.8 mmoles) of triethylamine in 25 ml of methylene chloride, and the mixture was stirred for 3.5 hours while the temperature was being returned to room temperature. To the reaction mixture was added 5.60 ml (37.4 mmoles) of 1,8-diazabicyclo[5,4,0]-7-undecene, and the mixture was stirred for 2.5 hours. The reaction mixture was poured into ice-dilute hydrochloric acid, and extracted with ether. The ether extract was washed with saturated aqueous sodium bicarbonate solution and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (150 g; n-hexane:ethyl acetate=5:1 to 3:1 v/v) to give 3.02 g of the captioned compound (19) as a colorless oil.

Workup

  1. customwas being returned to room temperature
  2. stirringthe mixture was stirred for 2.5 hours
  3. additionThe reaction mixture was poured into ice-dilute hydrochloric acid
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with saturated aqueous sodium bicarbonate solution and aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (150 g; n-hexane:ethyl acetate=5:1 to 3:1 v/v)

Sources & evidence

ORD record
ord-4db809372b634a7fa18d5f8331aeb656
Source dataset
uspto-grants-1991_09
Patent number
US05047564

Reaction notes

Loading…