Propionyl chloride → Methyl 4-cyclobutyl-2-methyl-5-(3-oxopentanoyl)benzoate

HRID 541450Notes

Reaction equation

[C:1]([C:4]1[C:5]([CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>O1CCCC1>[CH:15]1([C:5]2[C:4]([C:1](=[O:3])[CH2:2][C:29](=[O:32])[CH2:30][CH3:31])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:14])[CH:6]=2)[CH2:16][CH2:17][CH2:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 5-acetyl-4-cyclobutyl-2-methylbenzoate (compound 238.1, 500 mg, 2.03 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) at 0° C. was added dropwise a solution of LiHMDS (680 mg, 4.06 mmol, 2.00 equiv) in tetrahydrofuran (5 mL). After 30 min of stirring at 0° C., a solution of propanoyl chloride (280 mg, 3.03 mmol, 1.50 equiv) in tetrahydrofuran (5 mL) was added dropwise. The resulting mixture was stirred for 3 h at 15° C., and then concentrated under reduced pressure. The residue was diluted with 40 mL of ethyl acetate, washed with of brine (3×40 mL), dried (Na2SO4), and concentrated under reduced pressure. This resulted in 500 mg (crude) of the title compound as a brown oil.

Workup

stirringThe resulting mixture was stirred for 3 h at 15° C.
concentrationconcentrated under reduced pressure
additionThe residue was diluted with 40 mL of ethyl acetate
washwashed with of brine (3×40 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-fb2b25b7945240ee865024895b44ad71
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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