Potassium Carbonate → 6-(4-(4-Propylcyclohexyl)phenyl)-3,4-dihydrocoumarin

HRID 2115157

반응식

HRID 2115157 반응식
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].Br[C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][C:25](=[O:30])[CH2:24][CH2:23]2.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC.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>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[O:26][C:25](=[O:30])[CH2:24][CH2:23]4)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2667376-Bromochroman-2-oneHCID 31047104-(trans-4-Propylcyclohexyl)phenylboronic Acid

생성물 1

HCID 586608306-(4-(4-Propylcyclohexyl)phenyl)-3,4-dihydrocoumarin수율 32.6%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

4-(4-propylcyclohexyl)phenylboronic acid (1.3 g), 6-bromo-3,4-dihydrocoumarin (1.0 g), potassium carbonate (1.2 g), tetrakistriphenylphosphine-palladium (51 mg), and tetrabutylammonium bromide (10 mg) were suspended in DME (10 ml), and the suspension was stirred under reflux by heating for 3 hours. After completion of the reaction, the reaction mixture was added in ice water and extracted with toluene. An organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo and then subjected to isolation and purification by silica gel column chromatography, thereby obtaining a titled compound (500 mg). As a result of a variety of instrumental analyses, it was confirmed that this was the titled compound.

후처리

  1. temperatureunder reflux
  2. temperatureby heating for 3 hours
  3. customAfter completion of the reaction
  4. extractionextracted with toluene
  5. washAn organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated in vacuo
  8. customsubjected to isolation and purification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-c6aa1151a63a4378ad172fa609fefd4c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435455B2

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