3-Chloro-4-hydroxy-5-methoxybenzaldehyde → 3-(3-Chloro-4-hydroxy-5-methoxy-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one

HRID 552283

반응식

HRID 552283 반응식
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:27][CH3:28])[C:25]=1[OH:26])[CH:21]=O>C(O)C.Cl.C(O)(C)C.O>[Cl:17][C:18]1[CH:19]=[C:20]([CH2:21][CH2:9][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=2)=[O:10])[CH:23]=[C:24]([O:27][CH3:28])[C:25]=1[OH:26]

참가 물질

7

반응물 2

HCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehydeHCID 671661641-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanone

생성물 1

HCID 592489953-(3-Chloro-4-hydroxy-5-methoxy-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one수율 59.7%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

A solution of 1-(5-ethyl-4-phenyl-thiophen-2-yl)-ethanone (200 mg, 0.869 mmol) and 3-chloro-4-hydroxy-5-methoxybenzaldehyde (194 mg, 1.04 mmol) in ethanol (2 mL) and 5 N HCl in isopropanol (1 mL) is stirred at rt for 18 h. The dark green solution is diluted with water and extracted with EA. The organic extract is evaporated, dissolved in methanol (5 mL) and THF (5 mL) and treated with Pd/C (150 mg, 10% Pd). The slurry is hydrogenated under 1.8 bar of H2 for 18 h. The mixture is filtered over celite, the solvent is removed in vacuo and the crude product is purified by CC on silica gel eluting with heptane:EA 7:3 to give 3-(3-chloro-4-hydroxy-5-methoxy-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one (208 mg) as a colourless oil; LC-MS: tR=1.10 min, [M+1]+=401.12; 1H NMR (CDCl3): δ 7.58 (s, 1H), 7.46-7.30 (m, 5H), 6.83 (d, J=1.8 Hz, 1H), 6.67 (d, J=1.8 Hz, 1H), 3.88 (s, 3H), 3.16 (t, J=7.6 Hz, 2H), 2.98 (t, J=7.6 Hz, 2H), 2.91 (q, J=7.6 Hz, 2H), 1.30 (t, J=7.6 Hz, 3H).

후처리

  1. extractionextracted with EA
  2. extractionThe organic extract
  3. customis evaporated
  4. dissolutiondissolved in methanol (5 mL)
  5. additionTHF (5 mL) and treated with Pd/C (150 mg, 10% Pd)
  6. filtrationThe mixture is filtered over celite
  7. customthe solvent is removed in vacuo
  8. customthe crude product is purified by CC on silica gel eluting with heptane:EA 7:3

출처 및 근거

ORD 기록
ord-070df507d40d472e9b1ddeb4041c5f96
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951794B2

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