Hydrochloric Acid → HCID 19744888, compound

HRID 2254197Notes

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-66293a3ba78f4af3ba019d5e52f8e271
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05234951

Reaction notes

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