Ethyl trimethylsilylacetate → Ethyl 3-(oxazol-5-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

HRID 2246657Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(C)C.[O:21]1[C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)=[CH:30][CH:29]=2)=O)=[CH:24][N:23]=[CH:22]1>C1COCC1>[O:21]1[C:25]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)=[CH:32][CH:33]=2)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:24][N:23]=[CH:22]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of lithium bis(trimethylsilyl)amide (31.5 mmol, 1 M in THF) was added ethyl trimethylsilylacetate (31.5 mmol) dropwise at −78° C. After 20 minutes at −78° C., a solution of 5.2 (21 mmol) in THF (60 mL) was added dropwise and the reaction was maintained at −78° C. for 1.5 hours. The reaction was quenched saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), the organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated with silica gel under reduced pressure. The residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 5.3 (4.83 g, 14 mmol). MS ESI (pos.) m/e 344.2 (M+H).

Workup

customThe reaction was quenched saturated NH4Cl (aq)
temperaturewarmed to room temperature
extractionThe mixture was extracted with EtOAc (500 mL)
washthe organic phase was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated with silica gel under reduced pressure
customThe residue was chromatographed (silica gel, 1:1 EtOAc/hexane)

Sources & evidence

ORD record: ord-e1e70bfc41fc4b7ba55fd1b7479aeaa6
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687526B2

Reaction notes

Loading…