Triethylamine → 3-Oxocyclohex-1-en-1-yl 4-cyano-4-(3-fluorophenyl)-3-(4-fluorophenyl)butanoate

HRID 1525570Notes

Reaction equation

HRID 1525570 reaction equation
S(Cl)(Cl)=O.[C:5]([CH:7]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[CH:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=[O:11])#[N:6].[C:27]1(=O)[CH2:32][CH2:31][CH2:30][C:29](=[O:33])[CH2:28]1.C(N(CC)CC)C>ClCCl>[C:5]([CH:7]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[CH:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH2:9][C:10]([O:12][C:27]1[CH2:32][CH2:31][CH2:30][C:29](=[O:33])[CH:28]=1)=[O:11])#[N:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 24386Thionyl ChlorideHCID 148387394-Cyano-3-(4-fluorophenyl)-4-(3-fluorophenyl)butanoic acid

Product 1

HCID 712266463-Oxocyclohex-1-en-1-yl 4-cyano-4-(3-fluorophenyl)-3-(4-fluorophenyl)butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1.79 g (15 mmol) of thionyl chloride were added to 0.452 g (1.5 mmol) of 4-cyano-3-(4-fluorophenyl)-4-(3-fluorophenyl)butanoic acid, and the mixture was stirred at 80° C. for 1.5 h. Excess thionyl chloride was removed under reduced pressure. The reaction mixture concentrated in this manner (which contains acid chloride) was dissolved in 3 ml of dichloromethane and, at 0° C., added dropwise (about 30 min) to a mixture of 0.252 g (2.25 mmol) of 1,3-cyclohexanedione and 0.304 g (3 mmol) of triethylamine in dichloromethane (10 ml). After 3 h of stirring at 25° C., the solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure.

Workup

  1. customExcess thionyl chloride was removed under reduced pressure
  2. concentrationThe reaction mixture concentrated in this manner (which contains acid chloride)
  3. dissolutionwas dissolved in 3 ml of dichloromethane and, at 0° C.
  4. additionadded dropwise (about 30 min)
  5. stirringAfter 3 h of stirring at 25° C.
  6. customthe solvent was removed under reduced pressure
  7. washthe mixture was washed twice with in each case 25 ml of water
  8. dry with materialThe combined organic phases were dried over sodium sulphate
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c6cb295dbff6478aa73340936c1e856f
Source dataset
uspto-grants-2015_07
Patent number
US09084425B2

Reaction notes

Loading…