Methyl (trimethylsilyl)acetate → Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

HRID 2375742Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH3:19])=[O:17])(C)C.[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:29][CH:28]=1)=O>C1COCC1>[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:31][CH:32]=1)=[CH:15][C:16]([O:18][CH3:19])=[O:17]

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium bis(trimethylsilyl)amide (3.46 mmol, 1M in THF) was added dropwise to a solution of methyl trimethylsilylacetate (3.46 mmol) in THF (5 mL) at −78° C. After 20 minutes at −78° C., a solution of 10.2 (2.16 mmol) in THF (9 mL) was added dropwise and the reaction was maintained at −78° C. for 1.5 hours. The reaction was quenched with water and extracted with EtOAc. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 10.3. MS ESI (pos.) m/e 330.1 (M+1).

Workup

customThe reaction was quenched with water
extractionextracted with EtOAc
washThe organic phase was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was chromatographed (silica gel, 1:1 EtOAc/hexane)

Sources & evidence

ORD record: ord-9c43854d0d8344388626969d8e98f312
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465804B2

Reaction notes

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