3-Bromofuran → HCID 19047515, compound

HRID 742480Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][CH:8]=1.CN(OC)[C:14]([C:16]1[CH:20]=[CH:19][O:18][CH:17]=1)=[O:15]>CCOCC>[O:9]1[CH:10]=[CH:11][C:7]([C:14]([C:16]2[CH:20]=[CH:19][O:18][CH:17]=2)=[O:15])=[CH:8]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of n-butyllithium (2.5M, 28 mL, 0.07 mol) in 150 mL of ether at -78 ° C. was added a solution of 3-bromofuran (10 g, 0.0628 mol) in 30 mL of ether over a 20 min period and the mixture was stirred at -78° C. for 20 min. To the above mixture was added 3-(N-methyl-N-methoxycarbamoyl)furan (9.16 g, 0.059 mol) in 30 mL of ether over a 15 min period and the mixture was stirred at room temperature for 1/2 h. The reaction mixture was quenched with 200 mL of ammonium chloride solution, 500 mL of methylene chloride was added and the mixture was stirred. The organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was triturated with 100 mL of hexane/TBME (9:1). The solid product was filtered and washed with TBME to afford 7.5 g (78.3%) of di-(3-furyl)ketone.

Workup

stirringthe mixture was stirred at room temperature for 1/2 h
customThe reaction mixture was quenched with 200 mL of ammonium chloride solution, 500 mL of methylene chloride
additionwas added
stirringthe mixture was stirred
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customthe residue was triturated with 100 mL of hexane/TBME (9:1)
filtrationThe solid product was filtered
washwashed with TBME

Sources & evidence

ORD record: ord-c5a84b13b2a0486083e61ac834e25af2
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05554620

Reaction notes

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