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

HRID 1427716Notes

Reaction equation

HRID 1427716 reaction equation
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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-6eee88cae3c249c681b030cebb6d1055
Source dataset
uspto-grants-2015_01
Patent number
US08933256B2

Reaction notes

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