4-Methyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione → 4-Methyl-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione

HRID 714158노트

반응식

HRID 714158 반응식
[CH3:1][CH:2]([C:16](=[O:28])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1)[C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1>[Pd].C(OCC)(=O)C>[CH3:1][CH:2]([C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)[C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1

참가 물질

4

반응물 1

HCID 695017674-Methyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione

생성물 1

HCID 695017144-Methyl-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione수율 41.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

4-Methyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (6a, 0.20 g, 0.5 mmol) and palladium on activated carbon (0.25 g, 10%) were combined in ethyl acetate (100 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 2 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford an oil. The crude oil was twice chromatographed on silica gel with ethyl acetate/hexane to give a semi-solid. The crude semi-solid was distilled bulb to bulb to give 80 mg (38%) of a pale yellow oil; 1H NMR: δ enol form: 1.69 (s, 3H), 2.72 (m, 8H), 3.83 (s, 6H), 5.48 (s, 2H), 6.69 (m, 4H), 6.79 (d, 2H, J=7.5 Hz); keto form: 1.23 (d, 3H, J=7.2 Hz), 2.72 (m, 8H), 3.57 (q, 1H, J=7.0 Hz), 3.83 (s, 6H), 5.48 (s, 2H), 6.69 (m, 4H), 6.79 (d, 2H, J=7.5 Hz); 13C NMR: δ 12.5, 29.2, 43.3, 55.9, 61.4, 111.0, 114.2, 120.7, 132.4, 143.9, 146.3, 206.1; Exact mass calcd for C22H26O6: 386.1729, observed (M+H) 387.1783.

후처리

  1. customfor 2 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. customthe solvent evaporated
  5. customto afford an oil
  6. customThe crude oil was twice chromatographed on silica gel with ethyl acetate/hexane
  7. customto give a semi-solid
  8. distillationThe crude semi-solid was distilled bulb to bulb

출처 및 근거

ORD 기록
ord-dd1ef123397449bab44735f05587c5d5
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187397B2

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