Reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.CC(O)C.[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22](=[O:25])[CH2:23][Cl:24].Cl>C1(C)C=CC=CC=1.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.O.CCCCCC>[Cl:24][CH2:23][C@H:22]([C:21]1[CH:26]=[CH:27][CH:28]=[C:19]([Cl:18])[CH:20]=1)[OH:25]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
To a slurry solution of 143 mg (0.5 mmol) of (R)-1,1′-bi-2-naphthol in 10 ml of toluene was added 0.5 ml (0.5 mmol) of a 1.0 M hexane solution of triisobutylaluminum at room temperature, and the mixture was stirred at room temperature for 30 minutes. Thereto 1.52 ml (20 mmol) of 2-propanol was added and the mixture was stirred further at room temperature for 30 minutes. Thereto 1.89 g (10 mmol) of m-chlorophenacyl chloride was added and the mixture was stirred further at 50° C. for 4 hours. To the mixture were added 2 ml of 1N hydrochloric acid and 20 ml of water to conduct hydrolysis. The mixture was extracted with ethyl acetate and concentrated to obtain 2.424 g of an oily product. The obtained oil was analyzed by HPLC.
Workup
- stirringthe mixture was stirred further at room temperature for 30 minutes
- stirringthe mixture was stirred further at 50° C. for 4 hours
- customhydrolysis
- extractionThe mixture was extracted with ethyl acetate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-710ef65020cf4462ae757bd76cd4e720
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187966B1
Linked notes
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