N-methoxy-N-methyloxane-4-carboxamide → 1-(Tetrahydro-2H-pyran-4-yl)ethanone

HRID 2206635Notes

Reaction equation

CON(C)[C:4]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].[CH3:13][Mg]Br>O1CCCC1>[O:9]1[CH2:8][CH2:7][CH:6]([C:4](=[O:5])[CH3:13])[CH2:11][CH2:10]1

Participants

Conditions

Temperature: -25 °C

Procedure

To a solution of N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (3.5 g, 20.2 mmol) in tetrahydrofuran (30 mL) was added methylmagnesium bromide (12 mL, 36.4 mmol) at −65° C. under N2. The reaction was stirred at −65-15° C. for 3 hrs. Then the mixture was quenched by water, extracted with ethyl acetate. The organic layer was washed with 1 M HCl, saturated aqueous NaHCO3 and concentrated in vacuo to give 1-(tetrahydro-2H-pyran-4-yl)ethanone (1.9 g, 73.6%) as a yellow oil. 1H NMR (CDCl3, 400 M Hz) δ 4.01-3.97 (m, 2H), 3.45-3.39 (m, 3H), 2.57-2.49 (m, 1H), 1.80-1.71 (m, 2H), 1.70-1.62 (m, 2H).

Workup

customThen the mixture was quenched by water
extractionextracted with ethyl acetate
washThe organic layer was washed with 1 M HCl, saturated aqueous NaHCO3
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5550789e76c845c59582d07b6009213f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

Loading…