Acetic Acid → (E)-tert-butyl 2-(3-hydroxynaphthalene-2-carbonyl)-3-phenylprop-2-enoate

HRID 2263641Notes

Reaction equation

HRID 2263641 reaction equation
[OH:1][C:2]1[C:3]([C:12](=[O:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[OH:1][C:2]1[C:3]([C:12](/[C:13](=[CH:22]\[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)/[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[O:21])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 58264999HCID 58264999, compound

Product 1

HCID 58265003(E)-tert-butyl 2-(3-hydroxynaphthalene-2-carbonyl)-3-phenylprop-2-enoateYield 57%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to general procedure A using tert-butyl 3-(3-hydroxynaphthalen-2-yl)-3-oxopropanoate (286 mg, 1.0 mmol), benzaldehyde (100 μL, 1.00 mmol), 15.0 mL benzene, piperidine (10 μL, 0.10 mmol) and glacial acetic acid (5.7 μL, 0.10 mmol), refluxed for 4 h. Purified via recrystallization from hexanes/CH2Cl2, yielding 213 mg (57%) of yellow solid. mp=132-135° C.; IR (film) 2977.6; 1716.6; 1639.5; 1154.5 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.20 (bs, 1H), 8.19 (s, 1H); 7.96 (s, 1H), 7.70 (t, J=7.3 Hz, 2H), 7.51 (t, J=8.0 Hz, 1H), 7.40-7.25 (m, 7H), 1.38 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 201.9, 163.9, 157.1, 142.8, 138.7, 135.1, 132.8, 131.6, 130.8, 130.4, 130.2, 129.8, 129.2, 127.3, 126.6, 124.4, 121.7, 112.6, 83.0, 28.1; LRMS (electrospray): Mass calculated for C24H22O4 [M]+, 374.15. Found [M+23]+, 397.0.

Workup

  1. customPrepared
  2. temperaturerefluxed for 4 h
  3. customPurified via recrystallization from hexanes/CH2Cl2

Sources & evidence

ORD record
ord-8882a02393e04354bdbdd49c623ccc0c
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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