Water → Benzyl 1-methyl-4-oxocyclohexane-1-carboxylate

HRID 2060031

Reaction equation

C[Si](C)(C)O[CH:4]=[CH:5][CH:6]=[CH2:7].[CH3:10][C:11](=[CH2:22])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[OH2:23]>C(C1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1)C1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1>[CH3:22][C:11]1([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:7][CH2:6][C:5](=[O:23])[CH2:4][CH2:10]1

Participants

Conditions

Temperature: 200 °C

Procedure

2-(Trimethylsilyloxybutadiene (6.46 g, 45.4 mmol), phenylmethyl 2-methyl-2-propenoate (8.00 g, 45.4 mmol), and 4,4′-methanediylbis[2,6-bis(1,1-dimethylethyl)phenol] (0.019 g, 0.045 mmol) were combined together in a 20.0 mL microwave vessel and heated to 200° C. for 300 mins. Sample recovered and removed from vessel using THF (˜3×10 mL). The solvent was removed under reduced pressure and the residual oil taken up in 10% 2N HCl/THF (100 mL) and stirred overnight. After this time a clear solution formed, which was diluted with water (50 mL), partitioned into DCM (2×100 mL) and the organic layers separated, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified by FC over Silica (150 g: 5-10% EtOAc/iso-hex) to afford a clear oil. Confirmed by NMR to be phenylmethyl 1-methyl-4-oxocyclohexanecarboxylate (3.48 g, 11.30 mmol, 24.89% yield).

Workup

customSample recovered
customremoved from vessel
customThe solvent was removed under reduced pressure
customAfter this time a clear solution formed
custompartitioned into DCM (2×100 mL)
customthe organic layers separated
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed under reduced pressure
customThe residue was purified by FC over Silica (150 g: 5-10% EtOAc/iso-hex)
customto afford a clear oil

Sources & evidence

ORD record: ord-4577cba1a7964887a0e9fa342b134259
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278328B2

Linked notes

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