Potassium Phosphate, Tribasic → HCID 58897813, compound

HRID 2357866Notes

Reaction equation

HRID 2357866 reaction equation
CO[C:3]1([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[C:23]1([C:33]2[C:41]3[C:36](=[C:37]([OH:42])[CH:38]=[CH:39][CH:40]=3)[CH2:35][CH:34]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.[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>[C:23]1([C:33]2[C:41]3[C:36](=[C:37]([O:42][C:7]4[CH:8]=[CH:9][CH:10]=[C:11]5[C:6]=4[CH2:5][CH:4]=[C:3]5[C:13]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[CH:16]=[CH:15][CH:14]=4)[CH:38]=[CH:39][CH:40]=3)[CH2:35][CH:34]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27349362-Di-tert-butylphosphino-2'-(N,N-dimethylamino)biphenylHCID 58897783HCID 58897783, compoundHCID 58897788HCID 58897788, compound

Product 1

HCID 58897813HCID 58897813, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, to a mixture of 5.50 g (15.6 mmol) of 4-bromo-1-(1-naphthyl)-2,3-dihydro-1H-inden-1-yl methyl ether, 4.00 g (15.5 mmol) of 3-(1-naphthyl)-1H-inden-7-ol, 6.60 g (31.1 mmol) of K3PO4, and 150 ml of toluene, a mixture of 183 mg (0.32 mmol) of Pd(dba)2 and 212 mg (0.62 mmol) of N-{2′-[di(tert-butyl)phosphino][1,1′-biphenyl]-2-yl}-N,N-dimethylamine was added. The resulting mixture was stirred for 8 hours at 100° C. Then, 300 ml of water was added, the organic layer was separated, and the aqueous layer was extracted with 3×75 ml of CH2Cl2. The combined extract was dried over Na2SO4 and evaporated to dryness. The crude 1-(1-methoxy-4-{[1-methoxy-1-(1-naphthyl)-2,3-dihydro-1H-inden-4-yl]oxy}-2,3-dihydro-1H-inden-1-yl)naphthalene was purified using a short column with Silica Gel 60 (40-63 μm, d 50 mm, l 70 mm, eluant: CH2Cl2). This product was demethoxylated in a mixture of 170 ml of 16 M HCl and 170 ml of methanol for 7 hours at reflux. The crude product was extracted with 3×150 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 by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 300 mm, eluant:hexanes-CH2Cl2=5:1). Yield, 2.65 g (34%) of a white solid.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×75 ml of CH2Cl2
  4. extractionThe combined extract
  5. dry with materialwas dried over Na2SO4
  6. customevaporated to dryness
  7. customThe crude 1-(1-methoxy-4-{[1-methoxy-1-(1-naphthyl)-2,3-dihydro-1H-inden-4-yl]oxy}-2,3-dihydro-1H-inden-1-yl)naphthalene was purified
  8. additionThis product was demethoxylated in a mixture of 170 ml of 16 M HCl and 170 ml of methanol for 7 hours
  9. temperatureat reflux
  10. extractionThe crude product was extracted with 3×150 ml of CH2Cl2
  11. extractionThe combined extract
  12. washwas washed with 2×100 ml of water
  13. dry with materialdried over K2CO3
  14. customevaporated to dryness
  15. customThe analytically pure product was obtained by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 300 mm, eluant:hexanes-CH2Cl2=5:1)
  16. customYield

Sources & evidence

ORD record
ord-3c5fe5e9f9204e97861c3e0d84a3d8a3
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

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