Furfural → HCID 22120012, compound

HRID 1274065Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH:28]([C:30]1[O:31][CH:32]=[CH:33][CH:34]=1)=[O:29]>O1CCCC1.CCCCCC.[Cl-].[Na+]>[Cl:13][C:14]1[C:26]([CH:28]([C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)[OH:29])=[C:25]([Cl:27])[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

Conditions

Temperature: -75 °C

Procedure

At -20° C., 4.0 g (39.6 mmol) of diisopropylamine in 80 ml of tetrahydrofuran are treated for 15 min with 19 ml (30.4 mmol) of 1.6 M n-butyllithium solution in hexane. After cooling to -75° C., a solution of 7.5 g (30.4 mmol) of tert-butyl 2,4-dichlorobenzoate in 20 ml of tetrahydrofuran is added dropwise and the mixture is stirred at room temperature for 12 h. The reaction mixture is admixed with a solution of 2.9 g (30.2 mmol) of 2-formylfuran in 15 ml of tetrahydrofuran and stirred at room temperature for a further 12 h. The mixture is taken up in 300 ml of saturated aqueous sodium chloride solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 9.2 g; 1H-NMR, δ [ppm], (CDCl3): 1.6 (s), 3.6 (d), 6.2 (m), 6.3 (m), 7.4 (m), 7.7 (d), 7.4 (m), 7.5 (d)

Workup

stirringstirred at room temperature for a further 12 h
extractionextracted with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
filtrationfiltered

Sources & evidence

ORD record: ord-d2c931c7ed0b4bf4ac35bbcaa25575a8
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156702

Reaction notes

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