Potassium Carbonate → HCID 86751256, compound
Reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:7](=[O:10])([O-])[O-:8].[K+].[K+].[Br-].[K+]>CC(C)=O>[OH:8][C@@:7]1([O:10][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:5][CH:4]=[C:3]2[C:3]([CH:4]=[CH:5][CH:6]=[CH:2]2)=[C:2]1[C:4]1[C:5]2[C:3](=[CH:4][CH:5]=[CH:6][CH:6]=2)[CH:2]=[CH:2][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
The compounds (R)-(+)-2-hydroxy-2-pentoxy-1,1'-binaphthalene and (R)-(+)-2,2'-dipentoxy-1,1'-binaphthalene were prepared as follows. 1 g (3.49 mmol) (R)-(+)-2,2'-dihydroxy-1,1'-binaphthalene and 0.99 g (5 mmol) iodopentane were dissolved in 40 ml acetone while stirring. 6.99 g of potassium carbonate and 7.99 g (57.9 mmol) potassium bromide was added in one portion. After 24 hours stirring at room temperature, 1 g potassium carbonate was added. The reaction mixture was heated to 45° C. for 30 minutes. The excess potassium carbonate and potassium bromide were filtered and the solvent of the filtrate was removed with a rotavap. The crude product was purified by flash column with silica gel and dichloromethane as the eluent to obtain 370 mg of product consisting of 25% of the monosubstituted product and 56% of the disubstituted product.
Workup
- stirringAfter 24 hours stirring at room temperature
- filtrationThe excess potassium carbonate and potassium bromide were filtered
- customthe solvent of the filtrate was removed with a rotavap
- customThe crude product was purified by flash column with silica gel and dichloromethane as the eluent
Sources & evidence
- ORD record
- ord-08155b8d47d14daa94afc76606423e77
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05668614
Reaction notes
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