Ammonium Chloride → 5-Cyclopent-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

HRID 1516705노트

반응식

HRID 1516705 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.[C:27]1(B(O)O)[CH2:31][CH2:30][CH2:29][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.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>[C:27]1([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]([CH3:23])([CH3:22])[O:12]3)[CH2:31][CH2:30][CH2:29][CH:28]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 580029926-Formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

생성물 1

HCID 580029585-Cyclopent-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A solution of 550 mg (1.39 mmol) of 6-formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (Example 19A), 202 mg (1.81 mmol) of cyclopent-1-en-1-ylboronic acid, 112 mg (100 μmol) of tetrakis(triphenylphosphine)palladium and 503 mg (2.37 mmol) of potassium phosphate in 8 ml of degassed dioxane and stirred at 100° C. overnight. After cooling to room temperature, ammonium chloride solution is added and the mixture is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate, the solvent is then removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1).

후처리

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customthe solvent is then removed under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1)

출처 및 근거

ORD 기록
ord-3c2083a8486f4a57983c7fefd07e3e56
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227511B2

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