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

HRID 1405404

반응식

HRID 1405404 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 10129912Zinc(II) fluoride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a69e54d1aad34fee997f6f535585fb9b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916565B2

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