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

HRID 1516693
ノート
印刷プレビュー

反応式

HRID 1516693 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9a2438e669ef40e7979068b8b894861a
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08227511B2

反応ノート

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