Ethyl trimethylsilylacetate → Ethyl 3-(4-(benzyloxy)phenyl)-3-(3-methyl-3H-1,2,3-triazol-4-yl)acrylate

HRID 731192Notes

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.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:38]([CH3:42])[N:39]=[N:40][CH:41]=2)=O)=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:38]([CH3:42])[N:39]=[N:40][CH:41]=2)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:31][CH:30]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of lithium bis(trimethylsilyl)amide (22 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 73.3 (14.7 mmol) in THF (50 mL) was added dropwise, and the reaction was maintained at −78° C. for 4 hours. The reaction was quenched with saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), 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 73.4 (5.1 g, 14 mmol). MS ESI (pos.) m/e 364.1 (M+H).

Workup

customThe reaction was quenched with saturated NH4Cl (aq)
temperaturewarmed to room temperature
extractionThe mixture was extracted with EtOAc (500 mL)
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-d3b6dc36570846d99f11717850f3a53a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582803B2

Reaction notes

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