3-Bromofuran → tert-Butyl [2-(furan-3-yl)-2-oxoethyl]carbamate

HRID 2042928Notes

Reaction equation

[Li]CCCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.CON(C)[C:15](=[O:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C([O-])(O)=O.[Na+]>CCOCC.C1COCC1>[O:9]1[CH:10]=[CH:11][C:7]([C:15](=[O:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:8]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of n-BuLi (2.5 M in hexane, 7.68 mL) in anhydrous ether (10 mL) was added dropwise (over a 20-min period) a solution of 3-bromofuran (2.35 g, 16 mmol) in anhydrous THF (15 mL) under nitrogen atmosphere at −78° C. After stirring at −78° C. for 20 min, a solution of the Weinreb amide 45 (1.75 g, 8 mmol) in THF (15 mL) was added slowly to the mixture. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was poured into a saturated NaHCO3 solution and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4, filtered and evaporated under vacuum. The residue was further purified by silica column chromatography to provide the titled compound (671 mg, 37%). MNa+248.

Workup

temperatureto warm to room temperature
stirringstirred for 18 h
extractionextracted with EtOAc
dry with materialThe organic phase was dried over anhydrous MgSO4
filtrationfiltered
customevaporated under vacuum
customThe residue was further purified by silica column chromatography

Sources & evidence

ORD record: ord-80c94e46c7d7412fac6e9ad6027c833a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586550B2

Reaction notes

Loading…