Benzoic Acid → HCID 20147155, compound

HRID 569478Notes

Reaction equation

HRID 569478 reaction equation
[C:1]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:22]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1C=CC=CC=1.CCOCC.O>[C:1]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:22]([O:30][CH2:31][CH3:32])=[O:29])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 201471503-(Tridec-1-yn-1-yl)pyridine-4-carbaldehyde

Product 1

HCID 20147155HCID 20147155, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-(1-tridecynyl)pyridine-4-carboxaldehyde (7.13 g, 25 mmole, from Example 1), diethyl malonate (4.12 g), benzoic acid (0.145 g) and piperidine (0.18 ml) in benzene (45 ml) was refluxed under conditions of water removal for 24 hours. After cooling, ether was added and the solution was washed with dilute sodium bicarbonate solution and dried. Evaporation and distillation of excess diethyl malonate under reduced pressure afforded an oil which on silica gel chromatography gave 4.90 g (46%) of the title compound as a pale yellow oil, bp0.1 250° C. (Kugelrohr), νmax (film) 2930, 2850, 2220, 1730, 1640, 1250, 1215 cm-1 ; δ(CDCl3) 0.83 (3H, distorted t, terminal CH3), 1.12-1.65 (24H, m, ester CH3 +alkylene envelope), 2.43 (2H, t, J 6 Hz, CH2C≡C), 4.22 (2H, q, J 7 Hz, ester CH2), 4.30 (2H, q, J 7 Hz, ester CH2), 7.25 (1H, d, J 5 Hz, C-5H), 7.99 (1H, s, CH=C), 8.42 (1H, d, J 5 Hz, C-6H), 8.63 (1H, s, C-2H).

Workup

  1. temperatureAfter cooling
  2. washthe solution was washed with dilute sodium bicarbonate solution
  3. customdried
  4. customEvaporation and distillation of excess diethyl malonate under reduced pressure
  5. customafforded an oil which on silica gel chromatography

Sources & evidence

ORD record
ord-a46a94c9665d45b6adbd1b7b49be5a84
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Reaction notes

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