3-Bromofuran → HCID 19047515, 화합물

HRID 742480노트

반응식

HRID 742480 반응식
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

참가 물질

5

반응물 3

HCID 891643-BromofuranHCID 10487090N-methoxy-N-methylfuran-3-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 19047515HCID 19047515, 화합물수율 78.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c5a84b13b2a0486083e61ac834e25af2
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554620

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