Acetonitrile → 3-Phenoxybenzyl 2-{4-(methoxycarbonylmethyloxy)phenyl}-2-methylpropyl ether

HRID 975533Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.[H-].[Na+].C(#N)C.Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>C(OCC)(=O)C>[CH3:37][O:36][C:34]([CH2:33][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=2)=[CH:6][CH:7]=1)=[O:35]

Participants

Conditions

Temperature: 60 °C

Procedure

3-Phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether (3.0 g), 0.36 g of sodium hydride and 20 ml of acetonitrile were heated under reflux for about 20 minutes, followed by the dropwise addition of 2 ml of methyl bromoacetate at room temperature. The resulting mixture was stirred at 60° C. for 20 minutes. After concentration of the reaction mixture, about 50 ml of ethyl acetate were added to the concentrate, followed by washing with water, drying and concentration. The resulting concentrate was fractionated and purified by chromatography on a silica gel column, whereby 3.0 g of 3-phenoxybenzyl 2-{4-(methoxycarbonylmethyloxy)phenyl}-2-methylpropyl ether were obtained.

Workup

temperatureunder reflux for about 20 minutes
washby washing with water
customdrying
concentrationconcentration
concentrationThe resulting concentrate
custompurified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-1b25b21ad460477f8a9e05a02affe9d9
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608104

Reaction notes

Loading…