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

HRID 1525570ノート

反応式

HRID 1525570 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c6cb295dbff6478aa73340936c1e856f
出典データセット
uspto-grants-2015_07
特許番号
US09084425B2

反応ノート

読み込み中…