Ammonium Chloride → HCID 13537257, compound
Reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH2:29][CH:30]=[O:31])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1)[CH3:18].[NH4+].[Cl-]>C(OCC)C>[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH2:29][CH:30]([OH:31])[CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:9]=3)[CH2:27][CH2:28]2)=[CH:22][CH:21]=1)[CH3:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A Grignard reagent prepared from 3-phenoxybenzyl bromide (0.98 g), magnesium turnings (0.1 g) in dry diethyl ether (15 ml) under an atmosphere of nitrogen, is cooled with vigorous stirring to -78° C. To this is added a solution of 1-(4-ethoxyphenyl)-1-(2-oxoethyl)-cyclopropane (0.5 g) in diethyl ether (15 ml) over 5 min. The resulting mixture is allowed to warm up to room temperature over 1 h. Saturated NH4Cl solution is added and the mixture extracted with diethyl ether (x3), dried and the solvent evaporated under reduced pressure. The product is purified by t.l.c. on silica eluted with 10% diethyl ether in petroleum ether (b.p. 60°-80° C.). Yield 0.25 g, nD 1.5444.
Workup
- temperatureis cooled
- temperatureto warm up to room temperature over 1 h
- extractionthe mixture extracted with diethyl ether (x3)
- customdried
- customthe solvent evaporated under reduced pressure
- customThe product is purified by t.l.c
- washon silica eluted with 10% diethyl ether in petroleum ether (b.p. 60°-80° C.)
Sources & evidence
- ORD record
- ord-123436258846482aaf49c5f3d09bdbe0
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04713392
Reaction notes
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