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

HRID 1427716ノート

反応式

HRID 1427716 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6eee88cae3c249c681b030cebb6d1055
出典データセット
uspto-grants-2015_01
特許番号
US08933256B2

反応ノート

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