Ammonium Chloride → 4-(2-Methoxy-ethyl)-1-methyl-2-oxa-bicyclo[2.2.2]octan-3-one

HRID 2092655Notes

Reaction equation

[CH3:1][Mg]Br.C(O[C:7]([C:9]1([CH2:16][CH2:17][O:18][CH3:19])[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)=[O:8])C.[NH4+].[Cl-]>C1COCC1>[CH3:19][O:18][CH2:17][CH2:16][C:9]12[CH2:10][CH2:11][C:12]([CH3:1])([CH2:13][CH2:14]1)[O:15][C:7]2=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Methylmagnesium bromide (3.0M in diethyl ether, 1.22 mL) was dissolved in THF (5 mL). The mixture was cooled to 0° C. and a solution of 1-(2-methoxy-ethyl)-4-oxo-cyclohexanecarboxylic acid ethyl ester (350 mg, obtained in example 1, step 2) in THF (5 mL) was added dropwise over a period of 5 minutes. The resulting mixture was stirred at 0° C. for 3 hours. The reaction mixture was poured into ice/water and acidified with sat. NH4Cl. The aqueous phase was extracted two times with ethyl acetate and the organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a colorless liquid (67 mg, 22%). 1H-NMR (8, CDCl3): 3.55 (t, 2H); 3.31 (s, 3H); 1.86 (t, 2H); 1.84-1.73 (m, 8H); 1.39 (s, 3H).

Workup

extractionThe aqueous phase was extracted two times with ethyl acetate
washthe organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record: ord-e828405b1c564094a2e4b2a00007ca71
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440710B2

Reaction notes

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