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

HRID 552297ノート

反応式

HRID 552297 の反応式
[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]

参加物

7

反応物 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 67165130HCID 67165130、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2e62083d42c24af3a404fe11b38316f0
出典データセット
uspto-grants-2011_05
特許番号
US07951794B2

反応ノート

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