Acetic Acid → HCID 53752561, compound

HRID 1871544Notes

Reaction equation

HRID 1871544 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18][C:19]([CH3:21])=[O:20].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH2:24]([O:23][C:17](=[O:22])[C:18]([C:19](=[O:20])[CH3:21])=[CH:10][C:9]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 8082Piperidine2×HCID 8868Ethyl AcetoacetateHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Product 1

HCID 53752561HCID 53752561, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3-Cyclopentyloxy-4-methoxybenzaldehyde (7 g, 31.8 mmol), ethyl acetoacetate (4.13 g, 31.8 mmol), piperidine (275 mg, 3.18 mmol) and glacial acetic acid (100 mg) in toluene (350 ml) was heated at reflux with a Dean-Stark trap for 2 days, during which time, at regular intervals, further additions of piperidine (4×275 mg) and glacial acetic acid (4×100 mg) were made. The reaction mixture was then diluted with water and extracted with methylene chloride (3×150 ml), dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2 ; EtOAc:hexane (1:9)) affordedethyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-2-acetyl-prop-2-enoate (2 g, 19%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. extractionextracted with methylene chloride (3×150 ml)
  3. dry with materialdried over Na2SO4
  4. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-4180c844b4b3411e9907084e550c182f
Source dataset
uspto-grants-2000_08
Patent number
US06103749

Reaction notes

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