2-Naphthalenecarboxaldehyde → HCID 59595153, compound

HRID 2263642Notes

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[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH:28]=O.C([O-])(=O)C.[NH2+]1CCCCC1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](/[C:9](=[CH:28]\[C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=1)/[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:17]

Participants

Conditions

Temperature: 22 °C

Procedure

Prepared according to general procedure B using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (259 mg, 1.1 mmol), 2-naphthaldehyde (172 mg, 1.1 mmol), 12.0 mL toluene, piperidinium acetate (2.2 mL, 0.025M in toluene) and sodium sulfate (2.3 g), stirred at 22° C. for 7 d. Purified via recrystallization from hexanes/CH2Cl2, yielding 240 mg (58%) of beige crystals. mp=111-112° C.; IR (film) 2978.0; 1712.8; 1624.1; 1154.1 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.97 (bs, 1H); 8.02 (s, 1H); 7.91 (s, 1H); 7.79 (d, J=7.6 Hz, 1H); 7.78 (d, J=7.3 Hz, 1H); 7.70 (d, J=8.5 Hz, 1H); 7.58 (dd, J=8.0, 2.5 Hz, 1H); 7.51-7.46 (m, 3H); 7.37 (dd, J=8.5, 1.5 Hz, 1H); 7.05 (d, J=8.2 Hz, 1H); 6.81 (t, J=7.3 Hz, 1H); 1.44 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 201.9, 163.9, 162.9, 142.4, 137.3, 134.1, 133.2, 132.05, 132.03, 131.6, 130.6, 129.0 (x2), 128.0, 127.9, 127.0, 125.9, 120.3, 119.6, 118.6, 82.8, 28.2; LRMS (electrospray): Mass calculated for C24H22O4 [M]+, 374.14. Found [M+23]+, 397.2.

Workup

customPrepared
customPurified via recrystallization from hexanes/CH2Cl2

Sources & evidence

ORD record: ord-2c9f23bb862f40b5a4d03ec013f003ac
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851640B2

Reaction notes

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