Sodium Carbonate → 6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methylindan-1-one

HRID 716468Notes

Reaction equation

HRID 716468 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:18])[C:6]2=[O:17].[C:19]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:28]=1)([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC.O>[C:13]([C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][CH:5]([CH3:18])[C:6]2=[O:17])=[C:2]([C:25]2[CH:24]=[C:23]([C:19]([CH3:21])([CH3:20])[CH3:22])[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=2)[C:10]=1[O:11][CH3:12])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 11470330(3,5-Di-tert-butylphenyl)boronic acidHCID 602106934-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

Product 1

HCID 712309426-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methylindan-1-oneYield 44.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 30.7 g (98.6 mmol) of 4-bromo-6-tertbutyl-5-methoxy-2-methylindanone, 30.6 g (128 mmol) 3,5-di-tert-butylphenylboronic acid, 29.7 g (280 mmol) of Na2CO3, 1.35 g (5.92 mmol; 6 mol. %) of Pd(OAc)2, 3.15 g (11.8 mmol; 12 mol. %) of PPh3, 130 ml of water, and 380 ml of 1,2-dimethoxyethane was refluxed for 12 h. Further on, the reaction mixture was quenched with water, solvents were evaporated. The residue was dissolved in 500 ml of dichloromethane, and this solution was washed by 500 ml of water. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was dried over Na2SO4, then evaporated to dryness. The crude product isolated from the residue using flash chromatography on silica gel 60 (40-63 um, hexanes-dichloromethane=2:1, vol.) was then re-crystallized from n-hexane to give 18.5 g (43%) of a white solid.

Workup

  1. temperaturewas refluxed for 12 h
  2. customFurther on, the reaction mixture was quenched with water, solvents
  3. customwere evaporated
  4. dissolutionThe residue was dissolved in 500 ml of dichloromethane
  5. washthis solution was washed by 500 ml of water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was additionally extracted with 100 ml of dichloromethane
  8. extractionThe combined organic extract
  9. dry with materialwas dried over Na2SO4
  10. customevaporated to dryness
  11. customThe crude product isolated from the residue
  12. customwas then re-crystallized from n-hexane

Sources & evidence

ORD record
ord-b9e4156dc0cc46088184d8b37d8eff08
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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