Acetyl chloride → HCID 178477147, compound

HRID 379953Notes

Reaction equation

HRID 379953 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C@H:13]2[CH2:18][CH2:17][C@H:16]([S:19]([CH2:21][C:22]3C=CC(Cl)=CC=3)=O)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.N1C(C)=CC=CC=1C.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:42].C(=O)([O-])O.[Na+].C(N(CC)CC)C.C(Cl)(=O)C>O1CCCC1CC#N.C(Cl)Cl.C(OCC)(=O)C>[C:21]([S:19][C@H:16]1[CH2:17][CH2:18][C@H:13](/[CH:12]=[CH:11]/[CH:10]=[CH:9]/[C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:30])([F:29])[F:1])=[CH:4][CH:5]=2)[CH2:14][CH2:15]1)(=[O:42])[CH3:22]

Participants

10

Reactant 6

HCID 6367Acetyl chlorideHCID 79372,6-LutidineHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 178527209HCID 178527209, compound

Product 1

HCID 178477147HCID 178477147, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 4962721(Tetrahydrofuran-2-yl)acetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In 11 ml of a mixed solvent of tetrahydrofuran-acetonitrile (8:3) were dissolved 178 mg (0.39 mmol) of 4-chlorobenzyl trans-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexyl sulfoxide, and 168 mg (1.57 mmol) of 2,6-lutidine were added to the solution. To the mixture were added 165 mg (0.79 mmol) of trifluoroacetic anhydride with stirring at 0° C. After 3 minutes, an aqueous sodium hydrogencarbonate solution was added to the mixture, followed by extraction with ethyl acetate. The oily residue obtained by evaporation of the solvent was dissolved in 10 ml of methylene chloride, and 119 mg (1.17 mmol) of triethylamine were added to the mixture at 0° C., followed by addition of 62 mg (0.79 mmol) of acetyl chloride to the resulting mixture. After 1 hour, the reaction mixture was diluted with ethyl acetate and washed with an aqueous sodium hydrogencarbonate solution and an aqueous NaCl solution. After the mixture was dried, the crude product obtained by evaporation of the solvent was subjected to column chromatography using 5 g of silica gel and eluted with a mixed solvent of methylene chloride-hexane (1:1), followed by purification over Rover column [GrosseB, a mixed solvent of ethyl acetate-hexane (1:19)] to obtain 98 mg (yield: 70w) of the title compound having a melting point of 113 to 115° C.

Workup

  1. additionwere added to the solution
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe oily residue obtained by evaporation of the solvent
  4. waitAfter 1 hour
  5. washwashed with an aqueous sodium hydrogencarbonate solution
  6. customAfter the mixture was dried
  7. customthe crude product obtained by evaporation of the solvent
  8. washeluted with a mixed solvent of methylene chloride-hexane (1:1)
  9. customfollowed by purification over Rover column [GrosseB

Sources & evidence

ORD record
ord-9103742000fc47f38d3e84966e425369
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Reaction notes

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