Isobutyraldehyde trimethylsilyl enol ether → Benzyl 3-methoxy-4-(2-methyl-1-oxopropan-2-yl)benzoate

HRID 1405404

Reaktionsgleichung

Br[C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][C:3]=1[O:18][CH3:19].C[Si](C)(C)[O:22][CH:23]=[C:24]([CH3:26])[CH3:25]>[F-].[F-].[Zn+2].CN(C=O)C>[CH3:19][O:18][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:2]=1[C:24]([CH3:26])([CH3:25])[CH:23]=[O:22])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a flask purged with nitrogen was added Pd(tBu3P)2 (26 mg, 0.050 mmol), ZnF2 (52 mg, 0.50 mmol) and DMF (4 mL). The reaction mixture was allowed to stir for 10 minutes before benzyl 4-bromo-3-methoxy-benzoate (323 mg, 1.01 mmol) was added followed by trimethyl(2-methylprop-1-enoxy)silane (277 μL, 1.51 mmol). The reaction was heated at 80° C. overnight. The crude mixture was quenched with brine and extracted with EtOAc 3 times. The organic layer was dried over sodium sulfate and the solvent was evaporated to give benzyl 3-methoxy-4-(2-methyl-1-oxopropan-2-yl)benzoate. ESI-MS m/z calc. 312.4, found 313.4 (M+1)+; Retention time: 3.27 minutes (4 min run).

Aufarbeitung

customTo a flask purged with nitrogen
additionwas added
customThe crude mixture was quenched with brine
extractionextracted with EtOAc 3 times
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag: ord-a69e54d1aad34fee997f6f535585fb9b
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08916565B2

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