Benzaldehyde → Dalosirvat

HRID 623795

반응식

HRID 623795 반응식
C(N(CC)CC)C.[CH:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:16]1[CH2:21][CH2:20][O:19][C:18]2[CH:22]=[C:23]([C:26](=[O:32])[CH2:27][CH2:28]N(C)C)[CH:24]=[CH:25][C:17]1=2>O1CCOCC1.[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[O:16]1[CH2:21][CH2:20][O:19][C:18]2[CH:22]=[C:23]([C:26](=[O:32])[CH2:27][CH2:28][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:15])[CH:24]=[CH:25][C:17]1=2

참가 물질

6

반응물 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 28250181-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(dimethylamino)propan-1-one

생성물 1

HCID 56837361Dalosirvat수율 12%

시약·촉매·용매 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide촉매HCID 312751,4-Dioxane용매2회

반응 조건

온도
95 °C

실험 절차

Triethylamine (3.61 mmol) and benzaldehyde (4.3 mmol) in dry dioxane (10 mL) was added to a solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino)propan-1-one (XVI) (5.4 mmol) and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (0.43 mmol) in dioxane heated at 95° C. under nitrogen. The solution was further heated overnight at 95° C. The solution was cooled and excess solvent was evaporated under vacuum. The residue was partitioned between CH2Cl2 and water. The organic phase was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate in hexane gradient to yield 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione 1 as a white solid (12% yield). 1H NMR (DMSO-d6, 400 MHz): δ ppm 3.33-3.37 (m, 4H), 4.29 (m, 2H), 4.34 (m, 2H), 6.98 (m, 1H), 7.48 (m, 1H), 7.55 (m, 3H), 7.64 (m, 1H), 8.00-8.02 (m, 2H); ESIMS found C18H16O4 m/z 297 (M+H).

후처리

  1. temperatureThe solution was cooled
  2. customexcess solvent was evaporated under vacuum
  3. customThe residue was partitioned between CH2Cl2 and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate in hexane gradient

출처 및 근거

ORD 기록
ord-4a814f52ad9f4935a1248735ec214dc4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303010B2

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