Benzaldehyde → (E)-tert-butyl 2-(2-hydroxyphenylcarbonyl)-3-phenylprop-2-enoate

HRID 2263635Notes

Reaction equation

HRID 2263635 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1CCCCC1.C(O)(=O)C.C1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](/[C:9](=[CH:18]\[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:17]

Participants

6

Reactant 2

HCID 240BenzaldehydeHCID 16125894Tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate

Product 1

HCID 16125842(E)-tert-butyl 2-(2-hydroxyphenylcarbonyl)-3-phenylprop-2-enoateYield 83.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

Prepared according to general procedure A using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (618 mg, 2.6 mmol), benzaldehyde (265 μL, 2.6 mmol), 12.0 mL benzene, piperidine (13 μL, 0.13 mmol) and glacial acetic acid (7.5 μL, 0.13 mmol), refluxed for 2 h. Purified via recrystallization from hexanes/CH2Cl2, yielding 708 mg (83%) of 5 as clear crystals. mp=109-110° C.; IR (film) 2978.4; 1737.4; 1692.4; 1643.3; 1145.8 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.92 (bs, 1H), 7.86 (s, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.49 (t, J=8.4 Hz), 1H, 7.37-7.28 (m, 5H), 7.04 (d, J=8.4 Hz. 1H), 6.83 (t, J=7.3 Hz, 1H), 1.42 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 201.6, 163.8, 162.8, 142.3, 137.2, 133.0, 131.9, 131.6, 130.7, 130.3, 129.1, 120.2, 119.6, 118.5, 82.8, 28.1; LRMS (electrospray): Mass calculated for C20H20O4, [M]+, 324.13. Found [M+23]+, 347.3. 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 2 h
  3. customPurified via recrystallization from hexanes/CH2Cl2

Sources & evidence

ORD record
ord-846d837f3feb482ab7a8d13d0cdf516d
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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