Toluene → HCID 15314501, compound

HRID 1276700Notes

Reaction equation

HRID 1276700 reaction equation
[H-].[Na+].C1(C)C=CC=CC=1.[CH:10]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11]1.Br[C:17]1[C:18]2[C:23]([CH:24]=[C:25]3[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]3)=[CH:22][CH:21]=[CH:20][CH:19]=2>[Cl-].[Na+].O.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>[CH:10]1([O:15][C:17]2[C:30]3[C:25]([CH:24]=[C:23]4[C:18]=2[CH:19]=[CH:20][CH:21]=[CH:22]4)=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

9

Reactant 4

HCID 1140Toluene2×HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 740629-Bromoanthracene

Product 1

HCID 15314501HCID 15314501, compoundYield 68.6%

Reagents, catalysts & solvents 4

HCID 4189906(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

An oven dried Schlenk tube equipped with a teflon coated stir bar was charged with NaH (60% dispersion in mineral oil, 60 mg, 1.50 mmol), placed under vacuum and back-filled with argon. To this was added toluene (2 mL) and cyclopentanol (109 μL, 0.90 mmol). The mixture was heated at 70° C. for 15 min at which time 9-bromoanthracene (193 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 were added. The mixture was heated at 100° C. under an atmosphere of argon. After 20 hours diethyl ether (30 mL) and brine (30 mL) were added. The organic layer was separated 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 (99:1 hexanes:ethyl acetate) to afford 9-anthryl cyclopentyl ether (135 mg, 68% yield) as a yellow solid

Workup

  1. customAn oven dried Schlenk tube
  2. customequipped with a teflon coated stir bar
  3. additionback-filled with argon
  4. additionwere added
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. customThe drying agent was removed by filtration
  8. concentrationthe mother liquor concentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica gel (99:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-efbd8a7b7207479c8863edfecbc5b250
Source dataset
uspto-grants-2000_12
Patent number
US06166226

Reaction notes

Loading…