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

HRID 1525570노트

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HRID 1525570 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c6cb295dbff6478aa73340936c1e856f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09084425B2

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