Ethanol → Ethyl 5-propyl-2-(3',4',5'-trifluoro-3-hydroxybiphenyl-4-yl)cyclohexanecarboxylate

HRID 1672103ノート

反応式

HRID 1672103 の反応式
[CH2:1]([CH:4]1[CH2:27][C:8]2[C:9](=[O:26])[O:10][C:11]3[C:16]([C:7]=2[CH2:6][CH2:5]1)=[CH:15][CH:14]=[C:13]([C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=1)[CH:12]=3)[CH2:2][CH3:3].[CH2:28](O)[CH3:29].[O-:31]CC.[Na+].O>C1COCC1.[Pd]>[CH2:1]([CH:4]1[CH2:27][CH:8]([C:9]([O:10][CH2:28][CH3:29])=[O:26])[CH:7]([C:16]2[CH:15]=[CH:14][C:13]([C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=3)=[CH:12][C:11]=2[OH:31])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

参加物

7

反応物 4

HCID 702EthanolHCID 962WaterHCID 2723922Sodium ethoxideHCID 166567888-Propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

生成物 1

HCID 67351318Ethyl 5-propyl-2-(3',4',5'-trifluoro-3-hydroxybiphenyl-4-yl)cyclohexanecarboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

10 g (26.9 mmol) of 8-propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one from Example 1 (1.2.) are dissolved in THF and hydrogenated to cessation in the presence of palladium/active carbon catalyst. The mixture is subsequently filtered, the solvent is removed under reduced pressure, and the residue is dissolved in abs. ethanol and, after addition of 5.5 g (80.7 mmol) of sodium ethoxide, refluxed overnight. After addition of water, the mixture is acidified, the solution is extracted with MTB ether and dried over sodium sulfate. The solvent is removed under reduced pressure, and the crude product is purified by crystallisation, giving ethyl 5-propyl-2-(3′,4′,5′-trifluoro-3-hydroxybiphenyl-4-yl)cyclohexanecarboxylate.

後処理

  1. filtrationThe mixture is subsequently filtered
  2. customthe solvent is removed under reduced pressure
  3. dissolutionthe residue is dissolved in abs
  4. temperaturerefluxed overnight
  5. extractionthe solution is extracted with MTB ether
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe crude product is purified by crystallisation

出典と根拠

ORDレコード
ord-2785fe46b87744e1b53f4fac9cc01ac2
出典データセット
uspto-grants-2011_08
特許番号
US07998541B2

反応ノート

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