Benzaldehyde → Dalosirvat

HRID 1410275ノート

反応式

HRID 1410275 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 56837361Dalosirvat収率 12%

試薬・触媒・溶媒 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
95 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f08142d7d93549878b565ec913dcadf6
出典データセット
uspto-grants-2014_12
特許番号
US08921413B2

反応ノート

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