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Potassium Carbonate → 5-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

HRID 1516693
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HRID 1516693 반응식
FC(F)(F)S(O[C:7]1[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=[C:13]2[C:8]=1[C:9](=[O:24])[CH2:10][C:11]([CH3:23])([CH3:22])[O:12]2)(=O)=O.[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:7]2[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:20])[CH3:21])[CH:14]=[C:13]3[C:8]=2[C:9](=[O:24])[CH2:10][C:11]([CH3:22])([CH3:23])[O:12]3)=[CH:30][CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2856454-Fluorophenylboronic acidHCID 580029926-Formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

생성물 1

HCID 580030235-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 312751,4-Dioxane용매

실험 절차

A solution of 800 mg (2.03 mmol) of 6-formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (Example 19A), 369 mg (2.64 mmol) of 4-fluorophenyl-boronic acid, 164 mg (142 μmol) of tetrakis(triphenylphosphine)palladium and 731 mg (3.45 mmol) of potassium carbonate and 10 ml of degassed dioxane is stirred at 100° C. overnight. After cooling to room temperature, ammonium chloride solution is added and the mixture is extracted twice with ethyl acetate. After drying of the combined organic phases over sodium sulfate, the solvent is removed under reduced pressure and the residue is purified by column chromatography (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 20:1).

후처리

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. dry with materialAfter drying of the combined organic phases over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customthe residue is purified by column chromatography (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 20:1)

출처 및 근거

ORD 기록
ord-9a2438e669ef40e7979068b8b894861a
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08227511B2

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