Acetic Acid → HCID 58264995, compound

HRID 2263640Notes

Reaction equation

HRID 2263640 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](/[C:10](=[CH:19]\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[O:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 59595151HCID 59595151, compound

Product 1

HCID 58264995HCID 58264995, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to general procedure A using tert-butyl 3-(2-hydroxy-4-methyphenyl)-3-oxopropanoate (250 mg, 1.0 mmol), benzaldehyde (100 μL, 1.00 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 154 mg (46%) of white solid. mp=92-95° C.; IR (film) 2977.9; 1718.2; 1627.9; 1155.0 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.95 (bs, 1H), 7.82 (s, 1H), 7.40 (d, J=9.6 Hz, 1H), 7.36-7.29 (m, 5H), 6.83 (s, 1H), 6.61 (d, J=8.0 Hz, 1H), 2.34 (s, 3H), 1.41 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 200.8, 163.9, 163.0, 149.0, 142.0, 133.0, 131.8, 131.7, 130.6, 130.3, 129.1, 120.9, 118.5, 118.0, 82.7, 28.1, 22.3; LRMS (electrospray): Mass calculated for C21H22O4 [M]+, 338.15. Found [M+23]+, 361.2. An NOE difference experiment was conducted for this compound and a positive NOE was seen for the alkene proton when the tert-butyl signal was irradiated and a positive NOE was seen for the tert-butyl signal upon irradiation of the alkene proton.

Workup

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

Sources & evidence

ORD record
ord-266c327f1a064cfca51f80bee728f703
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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