Cyclohexanecarboxaldehyde → HCID 16125893, compound

HRID 2263644Notes

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]1([CH:24]=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])(=O)C.[NH2+]1CCCCC1.S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH:18]1(/[CH:24]=[C:9](\[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[OH:1])=[O:17])/[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Reactant 4

HCID 16275Cyclohexanecarboxaldehyde

HCID 24436Sodium Sulfate

HCID 3014295Piperidinium acetate

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

Product 1

HCID 16125893HCID 16125893, compoundYield 50%

Conditions

Temperature: 22 °C

Procedure

Prepared according to general procedure B using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (236 mg, 1.0 mmol), cyclohexanecarboxaldehyde (120 μL, 1.0 mmol) 7.0 mL benzene, piperidinium acetate (2.0 mL, 0.025M in toluene) and sodium sulfate (2.1 g), stirred at 22° C. for 8 d. Purified via column chromatography with 5% EtOAc/hexanes, yielding 165 mg (50%) of a white solid. Rf=0.59 (10% ether/hexanes); mp=62-65° C.; IR (film) 2929.2; 1716.6; 1631.9; 1257.5; 1153.6 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.92 (s, 1H); 7.51-7.46 (m, 2H); 7.02 (d, J=8.2 Hz, 1H); 6.90-6.86 (m, 2H); 2.11 (m, 1H); 1.68-1.60 (m, 5H); 1.35 (s, 9H); 1.20-1.15 (m, 5H). 13C NMR (125 MHz, CDCl3) δ 200.8, 163.7, 162.6, 152.2, 136.9, 132.3, 124.6, 120.5, 119.2, 118.4, 82.3, 31.9, 28.5, 28.0, 25.8, 25.1; LRMS (electrospray): Mass calculated for C20H26O4 [M]+, 330.18. Found [M+23]+, 353.6.

Workup

customPrepared
customPurified via column chromatography with 5% EtOAc/hexanes

Sources & evidence

ORD record: ord-739603feaa8f4581bb96397545bc739d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851640B2

Reaction notes

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