Dimethylformamide → Methyl 4-[4-(5,8-dimethylnaphthalene-2-yl)-4-oxo-butanoyl]benzoate

HRID 277173Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:13]=[O:14])=[CH:7]2.[C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)(=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C.CN(C)C=O>O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](=[O:14])[CH2:17][CH2:16][C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18])=[CH:7]2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1.0 g of 5,8-dimethyl-2-naphthaldehyde, 1.2 g of methyl 4-acryloyl-benzoate, 0.28 g of 3-benzyl-5-(2-hydroxymethyl)-4-methylthiazolium chloride, 0.88 ml triethylamine and 20 ml N,N-dimethylformamide was heated under stirring at 70° C. for 3 hours. After the reaction solution was left standing for cooling to room temperature, water was added thereto, and the reaction solution was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated and the resulting crude crystals were washed with a mixed solvent of n-hexane and ethyl acetate to give 0.82 g of the title compound as colorless crystals.

Workup

temperaturewas heated
waitAfter the reaction solution was left
temperaturefor cooling to room temperature
extractionthe reaction solution was extracted with ethyl acetate (20 ml×3)
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThen, the filtrate was concentrated
washthe resulting crude crystals were washed with a mixed solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record: ord-846f97dcc71e43768acfd60278ef6283
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355669B1

Reaction notes

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