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

HRID 1405404

Reaction equation

HRID 1405404 reaction equation
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]

Participants

5

Reactant 2

HCID 99685Isobutyraldehyde trimethylsilyl enol etherHCID 58551480Benzyl 4-bromo-3-methoxybenzoate

Product 1

HCID 86668528Benzyl 3-methoxy-4-(2-methyl-1-oxopropan-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 10129912Zinc(II) fluorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-a69e54d1aad34fee997f6f535585fb9b
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Linked notes

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