Methanol → HCID 54287962, compound

HRID 1199861Notes

Reaction equation

HRID 1199861 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].Cl[CH:8]([CH2:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C:9]([F:13])=C(F)F.[CH3:24]O>>[F:13][C:9](=[CH:8][CH2:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])=[O:17])[C:1]([O:2][CH3:24])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 14043450HCID 14043450, compound

Product 1

HCID 54287962HCID 54287962, compoundYield 93.9%

Procedure

Potassium carbonate (6.0 g, 43.5 mmol) was added to a solution of 3.0 g (10.5 mmol) 3-chloro-4-phenylsulfonyl-1,1,2-trifluoro-1-butene in 30 mL methanol at room temperature in a 100 mL round-bottom flask. The resulting mixture was stirred for 12 hours at room temperature. After removal of solvent in vacuo, the residue was partitioned between 50 mL diethyl ether and 50 mL 10% aqueous hydrochloric acid. The whole mixture was stirred for one hour at room temperature. The ether layer was washed once with brine, then dried over anhydrous magnesium sulfate. Evaporation of solvent gave a crystalline product, which was purified by recrystallization from 30% ethyl acetate in hexanes to give 2.50 g (93.9%) methyl 2-fluoro-4-phenylsulfonyl-2butenoate as pale yellow crystals, mp 104.0°-105.0° C. 1H-NMR (300 MHz, CDCl3): δ 3.82(3H, s), 4.05(2H, dd, J=28 Hz), 6.17(1H, dt, J=8, 30 Hz), 7.55-7.9(phenyl protons 5H). Mass spectrum: m/e=258 (M+). 19F-NMR (CDCl3): φ 121.4(d, J=31.0 ). Anal.: Calcd. for C11H11FO4S: C, 51.16; H, 4.26. Found: C, 51.02; H, 4.37.

Workup

  1. customAfter removal of solvent in vacuo
  2. customthe residue was partitioned between 50 mL diethyl ether and 50 mL 10% aqueous hydrochloric acid
  3. stirringThe whole mixture was stirred for one hour at room temperature
  4. washThe ether layer was washed once with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of solvent
  7. customgave a crystalline product, which
  8. customwas purified by recrystallization from 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bdfbc7fd01eb4c5db77d3cb0aed55afa
Source dataset
uspto-grants-1990_02
Patent number
US04902835

Reaction notes

Loading…