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

HRID 1672103노트

반응식

HRID 1672103 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2785fe46b87744e1b53f4fac9cc01ac2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998541B2

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