Ethyl trimethylsilylacetate → Ethyl 3-(1-methyl-1H-imidazol-5-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

HRID 2246653Notes

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.[CH3:21][N:22]1[C:26]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[CH:31][CH:30]=2)=O)=[CH:25][N:24]=[CH:23]1>C1COCC1>[CH3:21][N:22]1[C:26]([C:27]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[CH:33][CH:34]=2)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:25][N:24]=[CH:23]1

Participants

Conditions

Temperature: -45 °C

Procedure

To a solution of lithium bis(trimethylsilyl)amide (6.8 mmol, 1 M in THF) was added ethyl trimethylsilylacetate (6.5 mmol) dropwise at −78° C. After 20 minutes at −78° C., a solution of 4.2 (5.9 mmol) in THF (20 mL) was added dropwise. The reaction was maintained at −78° C. for 3 hours and at −45° C. for 2 hours. The reaction was quenched with saturated NH4Cl (aq) at 0° C. and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford crude 4.3 (2.49 g). MS ESI (pos.) m/e 357.2 (M+H).

Workup

customThe reaction was quenched with saturated NH4Cl (aq) at 0° C.
temperaturewarmed to room temperature
extractionThe mixture was extracted with EtOAc (500 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-532d55fecd524d19b13749931a502df0
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687526B2

Reaction notes

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