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Sodium Bicarbonate → Rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

HRID 1516697
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HRID 1516697 반응식
Br[Mg][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]([CH:31]=[O:32])=[C:29]([CH:33]([CH3:35])[CH3:34])[CH:28]=[C:27]3[C:22]=2[C:23](=[O:38])[CH2:24][C:25]([CH3:37])([CH3:36])[O:26]3)=[CH:17][CH:16]=1.FC1C=CC(C2C(C=O)=C(CCC)C=C3C=2C(=O)CC(C)(C)O3)=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]([CH:31]([OH:32])[C:3]3[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=3)=[C:29]([CH:33]([CH3:34])[CH3:35])[CH:28]=[C:27]3[C:22]=2[C:23](=[O:38])[CH2:24][C:25]([CH3:36])([CH3:37])[O:26]3)=[CH:17][CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 580030235-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehydeHCID 87679748Rac-5-(4-fluorophenyl)-7-n-propyl-2,2-dimethyl-4-oxochroman-6-carbaldehydeHCID 178506384HCID 178506384, 화합물

생성물 1

HCID 58002959Rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

At −78° C., 2.35 ml (1.19 mmol) of a freshly prepared 0.5 M solution of bromo[4-(trifluoromethoxy)phenyl]magnesium in tetrahydrofuran are slowly added dropwise to a solution of 338 mg (990 μmol) of a 2:1 mixture of rac-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde (Example 20A) and rac-5-(4-fluorophenyl)-7-n-propyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde in 8 ml of tetrahydrofuran. The mixture is then allowed to thaw slowly to −20° C. and stirred at this temperature for 45 min. 10% strength sodium bicarbonate solution is then added, the mixture is extracted three times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution. The organic phases are dried over magnesium sulfate, the solvent is then removed under reduced pressure and the residue is purified by preparative HPLC (method 1).

후처리

  1. customthaw slowly to −20° C.
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customthe solvent is then removed under reduced pressure
  6. customthe residue is purified by preparative HPLC (method 1)

출처 및 근거

ORD 기록
ord-fd1be789860f412bb0e4e67410f33afd
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08227511B2

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