3-Buten-2-one, 4-methoxy- → HCID 178495556, compound

HRID 1430150Notes

Reaction equation

[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][O:12][CH:13]=[CH:14][C:15](=[O:17])[CH3:16].[CH3:18][C:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1>C1COCC1>[OH:23][C:22]([C:19]1([CH3:18])[CH2:21][CH2:20]1)=[CH:16][C:15](=[O:17])[CH:14]=[CH:13][O:12][CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

LiHMDS (1M in THF, 88 mL, 2 eq) is added dropwise to a cold (−78° C.) solution of 4-methoxy-3-buten-2-one (8.8 mL, 88 mmol, 2 eq) in THF (300 mL). After a 30 min stirring at −78° C., a solution of 1-methyl-cyclopropanecarbonyl chloride (Step 40.8) (5.19 g, 44 mmol) in THF (100 mL) is added. The resulting mixture is allowed to warm to rt over 2 h and quenched by addition of a saturated solution of NH4Cl. THF is removed under vacuum. The concentrated mixture is extracted with Et2O. The organic phase is washed with brine (2×150 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0→95:5) to afford 5.68 g of the title compound as a yellow oil: ESI-MS: 183.1 [M+H]+; TLC: Rf=0.32 (Hex/EtOAc, 9:1).

Workup

temperatureto warm to rt over 2 h
customquenched by addition of a saturated solution of NH4Cl
customTHF is removed under vacuum
extractionThe concentrated mixture is extracted with Et2O
washThe organic phase is washed with brine (2×150 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0→95:5)

Sources & evidence

ORD record: ord-7a5a226051094b93acff8a93fe4c6d32
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940771B2

Reaction notes

Loading…