Hydrochloric Acid → HCID 19744888, compound

HRID 1030682Notes

Reaction equation

[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=[C:4]([O:15][CH3:16])[C:3]=1[C:17](=[O:19])[CH3:18].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].Cl>CN(C)C=O>[CH2:8]([C:7]1[C:2]([O:1][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:3]([C:17](=[O:19])[CH3:18])[C:4]([O:15][CH3:16])=[CH:5][C:6]=1[O:13][CH3:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To 16.7 g of the so-obtained 2'-hydroxy-3'-isopentyl-4',6'-dimethoxyacetophenone and 1.5 g of sodium hydride was added 130 ml of dimethylformamide, and 9.9 g of methyl α-bromoacetate was further added and the mixture was stirred for 1.5 hours at 0° C. and for 2 hours at room temperature to effect reaction. After the reaction, the reaction mixture was made acidic by dilute hydrochloric acid, extracted with diethyl ether and filtered. The solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography [230-400 mesh silica gel, eluting solvent=n-hexane/ethyl acetate (4/1)] to obtain 14.9 g (yield=70.3%) of 3'-isopentyl-4',6'-dimethoxy-2'-methoxycarbonylmethoxyacetophenone.

Workup

additionwas further added
customreaction
customAfter the reaction
extractionextracted with diethyl ether
filtrationfiltered
customThe solvent was removed from the filtrate by distillation
washThe obtained residue was subjected to the silica gel column chromatography [230-400 mesh silica gel, eluting solvent=n-hexane/ethyl acetate (4/1)]

Sources & evidence

ORD record: ord-0e563822ba8b43a9ab70908c1f682eb7
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106871

Reaction notes

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