Potassium Phosphate, Tribasic → 1-Methoxy-4-[(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-2-methylindane

HRID 226204Notes

Reaction equation

HRID 226204 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[CH:6]2[O:11][CH3:12].[CH3:14][O:15][CH:16]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=2[CH2:18][CH:17]1[CH3:26].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1N(C)C)(C)(C)C>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>[CH3:12][O:11][CH:6]1[C:7]2[C:3](=[C:2]([O:25][C:20]3[CH:21]=[CH:22][CH:23]=[C:24]4[C:19]=3[CH2:18][CH:17]([CH3:26])[CH:16]4[O:15][CH3:14])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH:5]1[CH3:13]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27349362-Di-tert-butylphosphino-2'-(N,N-dimethylamino)biphenylHCID 64228144-Bromo-2-methyl-1-(methyloxy)-2,3-dihydro-1H-indeneHCID 598325291-Methoxy-2-methyl-4-indanol

Product 1

HCID 598325081-Methoxy-4-[(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-2-methylindane

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a mixture of 14.6 g (60.5 mmol) of 4-bromo-1-methoxy-2-methylindane, 10.8 g (60.5 mmol) of 1-methoxy-2-methyl-4-indanol, 38.5 g (181 mmol) K3PO4, and 200 ml of toluene, a mixture of 696 mg (1.21 mmol) Pd(dba)2 and 825 mg (2.42 mmol) of 2-di(tert-butyl)phosphino-2′-(N,N-dimethylamino)biphenyl was added under an argon atmosphere. This mixture was stirred for 14 hours at 100° C. Then, 300 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of CH2Cl2. The combined extract was washed with 2×100 ml of water, dried over K2CO3, and evaporated to dryness. The analytically pure product was obtained using flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, 1 400 mm, eluant:hexanes-dichloromethane=1:1, vol.). Yield 12.4 g (61%). On the evidence of NMR spectra, the product consists of a mixture of isomers.

Workup

  1. additionwas added under an argon atmosphere
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×100 ml of CH2Cl2
  4. extractionThe combined extract
  5. washwas washed with 2×100 ml of water
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness
  8. customThe analytically pure product was obtained
  9. additionOn the evidence of NMR spectra, the product consists of a mixture of isomers

Sources & evidence

ORD record
ord-917a21a3b1d24f33bd982427f622ab57
Source dataset
uspto-grants-2009_07
Patent number
US07557171B2

Reaction notes

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