Toluene → HCID 20457260, compound

HRID 1457395Notes

Reaction equation

HRID 1457395 reaction equation
[H-].[Na+].C1(C)C=CC=CC=1.[CH:10]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.Br[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C(OCC)C.O>[CH:10]1([O:16][C:26]2[C:27]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

9

Reactant 4

HCID 1140Toluene2×HCID 70011-BromonaphthaleneHCID 7966CyclohexanolHCID 24758Sodium hydride

Product 1

HCID 20457260HCID 20457260, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 4189906(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

An oven dried Schlenk tube equipped with a teflon coated stir bar was charged with NaH (40 mg, 1.50 mmol), toluene (2 mL) and cyclohexanol (94 μL, 0.90 mmol). The mixture was heated to 70° C. for 10 min under an atmosphere of argon. To this was added 1-bromonaphthalene (104 μL, 0.75 mmol), Pd2 (dba)3 (10.3 mg, 0.0113 mmol), (R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl (Tol-BINAP) (18.3 mg, 0.027 mmol), and 2 mL of toluene. The mixture was heated to 70° C. for 20 h at which time water (60 mL) and diethyl ether (60 mL) were added. The aqueous layer was separated and extracted with diethyl ether (60 mL). The organics were combined, washed with brine (60 mL) and dried over anhydrous MgSO4. The drying agent was removed by filtration and the mother liquor concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (50:1 hexanes:ethyl acetate) to afford 1-naphthyl cyclohexyl ether (101 mg, 60% yield) as a colorless oil.

Workup

  1. customAn oven dried Schlenk tube
  2. customequipped with a teflon coated stir bar
  3. additionwere added
  4. customThe aqueous layer was separated
  5. extractionextracted with diethyl ether (60 mL)
  6. washwashed with brine (60 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customThe drying agent was removed by filtration
  9. concentrationthe mother liquor concentrated in vacuo
  10. customThe crude product was purified by flash chromatography on silica gel (50:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-0c5a71c3037e4523a0d082db3287e027
Source dataset
uspto-grants-1998_12
Patent number
US05847166

Reaction notes

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