3,5-Dimethyl-4-hydroxybenzaldehyde → 3-(4-Hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-propyl-thiophen-2-yl)-propan-1-one

HRID 552297노트

반응식

HRID 552297 반응식
[C:1]1([C:7]2[CH:8]=[C:9]([C:15](=[O:17])[CH3:16])[S:10][C:11]=2[CH2:12][CH2:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:28])[C:26]=1[OH:27])[CH:22]=O>C(O)C.Cl.C(O)(C)C.O>[OH:27][C:26]1[C:25]([CH3:28])=[CH:24][C:21]([CH2:22][CH2:16][C:15]([C:9]2[S:10][C:11]([CH2:12][CH2:13][CH3:14])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=2)=[O:17])=[CH:20][C:19]=1[CH3:18]

참가 물질

7

반응물 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 67165130HCID 67165130, 화합물

생성물 1

HCID 592489793-(4-Hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-propyl-thiophen-2-yl)-propan-1-one수율 79%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

A solution of 1-(4-phenyl-5-propyl-thiophen-2-yl)-ethanone (450 mg, 1.84 mmol) and 3,5-dimethyl-4-hydroxybenzaldehyde (331 mg, 2.21 mmol) in ethanol (4 mL) and 5 N HCl in isopropanol (2 mL) is stirred at rt for 18 h. The dark 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 (100 mg, 10% Pd). The slurry is stirred under 1.8 bar of H2 for 16 h. The mixture is filtered, the solvent of the filtrate is removed in vacuo and the crude product is purified by CC prep. TLC plates with heptane:EA 2:1 to give 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-propyl-thiophen-2-yl)-propan-1-one (550 mg) as a colourless oil; LC-MS: tR=1.13 min; [M+1]+=379.20, 1H NMR (CDCl3): δ 7.56 (s, 1H), 7.45-7.28 (m, 5H), 6.85 (s, 2H), 4.48 (s, 1H), 3.17-3.10 (m, 2H), 2.96-2.89 (m, 2H), 2.87-2.80 (m, 2H), 2.21 (s, 6H), 1.74-1.64 (m, 2H), 0.94 (t, J=7.0 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 (100 mg, 10% Pd)
  6. filtrationThe mixture is filtered
  7. customthe solvent of the filtrate is removed in vacuo
  8. customthe crude product is purified by CC prep

출처 및 근거

ORD 기록
ord-2e62083d42c24af3a404fe11b38316f0
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951794B2

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