Acetyl chloride → acetic acid 4-(3-ethyl-4'-fluorobiphenyl-4-yl)-2,2,6-trimethyl-5-oxo-5,6-dihydro-2H-pyran-3yl ester

HRID 341677Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[C:14](=[O:15])[CH:13]([CH3:16])[O:12][C:11]([CH3:18])([CH3:17])[C:10]1=[O:19])[CH3:2].C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>ClCCl.O>[CH2:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[C:14](=[O:15])[CH:13]([CH3:16])[O:12][C:11]([CH3:18])([CH3:17])[C:10]=1[O:19][C:34](=[O:36])[CH3:35])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(3-ethyl-4′-fluorobiphenyl-4-yl)-2,2,6-trimethylpyran-3,5-dione (0.125 g, 0.35 mmol) in dichloromethane (5 ml) is added triethylamine (0.2 ml, 1.38 mmol) and the reaction mixture is cooled to 0° C. Acetyl chloride (0.22 g, 2.8 mmol) is added slowly at 0° C. and the mixture is stirred at 0° C. for 5 hours. The reaction mixture is diluted with water and extracted with dichloromethane (3×25 ml). The organic extracts are combined, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to afford acetic acid 4-(3-ethyl-4′-fluorobiphenyl-4-yl)-2,2,6-trimethyl-5-oxo-5,6-dihydro-2H-pyran-3yl ester (0.085 g) as a white solid.

Workup

extractionextracted with dichloromethane (3×25 ml)
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-d578487615404148b3975c1b0b891548
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895761B2

Reaction notes

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