Potassium Phosphate, Tribasic → 4-(4-tert-Butylphenyl)-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene

HRID 538861노트

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HRID 538861 반응식
Br[C:2]1[C:13]2[CH2:12][C:11]([CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:10][C:9]=2[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.[C:21]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.C1(C)C=CC=CC=1>[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:13]3[CH2:12][C:11]([CH2:14][CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)=[CH:10][C:9]=3[CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][CH2:6]3)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27343204-tert-Butylphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 666156084-Bromo-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene

생성물 1

HCID 866937974-(4-tert-Butylphenyl)-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

In argon atmosphere, a mixture of 34.6 g (105 mmol) of 4-bromo-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene, 22.4 g (126 mmol) 4-tert-butylphenylboronic acid, 66.8 g (315 mmol) of K3PO4, 1.21 g (21 mmol) of Pd(dba)2, 1.73 g (42 mmol) of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine and 350 ml of toluene was stirred for 12 h at 100° C. The resulting mixture was cooled to room temperature, and then 600 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The target product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes). Yield 24.0 g (62%).

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×100 ml of dichloromethane
  4. extractionThe combined organic extract
  5. dry with materialwas dried over Na2SO4
  6. customevaporated to dryness
  7. customThe target product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes)

출처 및 근거

ORD 기록
ord-d84dcb5bdd884e9fa3aabd107a14a6e5
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865848B2

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