Acetic Acid → HCID 57912479, compound

HRID 2263639Notes

Reaction equation

HRID 2263639 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](/[C:11](=[CH:20]\[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 57912472HCID 57912472, compound

Product 1

HCID 57912479HCID 57912479, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to general procedure A using tert-butyl 3-(2-hydroxy4-methoxyphenyl)-3-oxopropanoate (532 mg, 2.0 mmol), benzaldehyde (200 μL, 2.00 mmol), 12.0 mL benzene, piperidine (10 μL, 0.10 mmol) and glacial acetic acid (5.7 μL, 0.10 mmol), refluxed for 3 h. Purified via recrystallization from hexanes/CH2Cl2, yielding 321 mg (46%) of white solid. mp=105-107° C.; IR (film) 2977.5; 1712.8; 1624.0; 1155.6 cm−1; 1H NMR (500 MHz, CDCl3) δ 12.41 (bs, 1H), 7.81 (s, 1H), 7.41 (d, J=9.1 Hz, 1H), 7.37-7.25 (m, 5H), 6.46 (d, J=2.1 Hz, 1H), 6.34 (dd, J=8.8, 2.1 Hz, 1H), 3.83 (s, 3H), 1.42 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 199.4, 166.8, 165.8, 164.0, 141.8, 133.6, 133.1, 131.6, 130.5, 130.3, 129.1, 114.3, 108.4, 101.1, 82.6, 55.8, 28.1; LRMS (electrospray): Mass calculated for C21H22O5 [M]+, 354.14. Found [M+23]+, 377.5.

Workup

  1. customPrepared
  2. temperaturerefluxed for 3 h
  3. customPurified via recrystallization from hexanes/CH2Cl2

Sources & evidence

ORD record
ord-984f96aa540e4ff8a6cc34c341a50b3f
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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