Hydrochloric Acid → Benzyl 4-(2-cyclohexylethoxy)acetoacetate

HRID 397971Notes

Reaction equation

[H-].[Na+].[CH:3]1([CH2:9][CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[CH2:13][C:14](=[O:26])[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].Cl>C1COCC1>[CH:3]1([CH2:9][CH2:10][O:11][CH2:13][C:14](=[O:26])[CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 40 °C

Procedure

0.68 g (17.0 mmol) of sodium hydride (60% oily) was suspended in 7 ml of THF. 1.36 g (10.6 mmol) of 2-cyclohexylethanol was added to the obtained suspension at 0° C., and they were stirred at 40° C. for 30 minutes. 2.00 g (8.82 mmol) of benzyl 4-chloroacetoacetate was added to the obtained mixture at room temperature, and they were refluxed at 100° C. for 3 hours. 1 N hydrochloric acid was added to the reaction mixture. After the extraction with ethyl acetate, the organic layer was washed with 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=4/1) to obtain the title compound.

Workup

temperaturethey were refluxed at 100° C. for 3 hours
extractionAfter the extraction with ethyl acetate
washthe organic layer was washed with 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-7ed86e6a728b43a69e891c480f8699b4
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610717B2

Reaction notes

Loading…