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

Reaction equation

HRID 552297 reaction equation
[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]

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2e62083d42c24af3a404fe11b38316f0
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Linked notes

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