Naphthalene → HCID 86608435, compound
Reaction equation
[Na:1].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH3:17]>>[Na:1].[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH3:17]Participants
Procedure
3 g of sodium (130 mmol) are added to a solution of 3.6 g of naphthalene (28 mmol) in 30 ml of 1,2-dimethoxyethane. The reaction mixture is stirred at ambient temperature for 2 hours to form the sodium/naphthalene/1,2-dimethoxyethane solution. 14.8 ml (64 mmol) of the resulting solution are added, at a temperature of −70° C., to a solution of 3 g (6.1 mmol) of the compound obtained in the Step above in 55 ml of 1,2-dimethoxyethane. The colour of the solution changes from white to blue. Stirring is carried out for 30 minutes at −70° C., followed by hydrolysis using 100 ml of water. The mixture is then extracted with ethyl acetate, dried, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography on 200 g of silica (eluant: dichloromethane/ethanol/ammonia 90/10/1) to yield the expected product in the form of an oil.
Sources & evidence
- ORD record
- ord-5ac647056f10427392f59f1ae75938f1
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612061B2
Reaction notes
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