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

HRID 1405404

反応式

HRID 1405404 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10129912Zinc(II) fluoride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a69e54d1aad34fee997f6f535585fb9b
出典データセット
uspto-grants-2014_12
特許番号
US08916565B2

関連ノート

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