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Benzaldehyde → Methyl 2-(1-oxopropyl)-3-(4-fluorophenyl)-4-phenyl-4-oxobutanoate

HRID 2107087
Notes
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Reaction equation

HRID 2107087 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]=[C:7]([C:12](=[O:15])[CH2:13][CH3:14])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[CH:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.C(O)C>[I-].C[N+]1C(C)=C(CCO)SC=1.ClCCl>[O:15]=[C:12]([CH:7]([CH:6]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=1)[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:25])[C:8]([O:10][CH3:11])=[O:9])[CH2:13][CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 8471TriethylamineHCID 53755005Methyl 2-(4-fluorobenzylidene)-3-oxopentanoate

Product 1

HCID 23047461Methyl 2-(1-oxopropyl)-3-(4-fluorophenyl)-4-phenyl-4-oxobutanoateYield 28.5%

Reagents, catalysts & solvents 2

HCID 9838770
3,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodide
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-(4-fluorobenzylidene)-3-oxopentanoate (52.0 g), benzaldehyde (25.4 g), triethylamine (22 g), 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide (6.3 g) and ethanol (100 ml) was heated at reflux under nitrogen for 16 hours. The cooled mixture was diluted with dichloromethane, and washed with dilute hydrochloric acid (2N), with dilute aqueous sodium bicarbonate solution, and with water, and dried over magnesium sulphate. The solution was concentrated in vacuo and the residue was dissolved in hot methanol. The resulting off-white solid was filtered off, to give methyl 2-(1-oxopropyl)-3-(4-fluorophenyl)-4-phenyl-4-oxobutanoate (21.5 g), m.p. 104°-109° C. [Elemental analysis: C,70.1;H,5.42;F,5.58%; calculated: C,70.15;H,5.60; F,5.55%; I.R. 1749, 1738, 1716, 1708, 1679, 1508, 761, 697cm-1 [N.M.R. (in CDCl3): 0.81 and 1.08 (3H, two triplets, J=7 Hz), 1.80-2.04 and 2.46-2.80 (2H, two sets of multiplets), 3.53 and 3.68 (3H, two singlets), 4.58 and 4.62 (1H, two doublets, J=10 Hz), 5.39 and 5.42 (1H, two doublets, J=10 Hz), 6.96 (2H, t, J=8 Hz), 7.20- 7.60 (5H, m), 7.90-8.00 (2H, m)].

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 16 hours
  3. washwashed with dilute hydrochloric acid (2N), with dilute aqueous sodium bicarbonate solution
  4. dry with materialwith water, and dried over magnesium sulphate
  5. concentrationThe solution was concentrated in vacuo
  6. dissolutionthe residue was dissolved in hot methanol
  7. filtrationThe resulting off-white solid was filtered off

Sources & evidence

ORD record
ord-64489adf48f149e6a120ce7a2bd1f8c2
Source dataset
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04933350

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes