Acetic Acid → 3-(Bromoacetyl)-5-t-butyl-2-methyl-furan

HRID 2298626

반응식

HRID 2298626 반응식
[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7](C(Cl)=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si](C=[N+]=[N-])(C)C.[BrH:21].[C:22]([OH:25])(=O)[CH3:23]>C(#N)C>[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7]([C:22](=[O:25])[CH2:23][Br:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 27984945-(Tert-Butyl)-2-Methylfuran-3-Carbonyl Chloride

생성물 1

HCID 120258983-(Bromoacetyl)-5-t-butyl-2-methyl-furan수율 77%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 1 g (5 mmol) of 5-(tert-butyl)-2-methylfuran-3-carbonyl chloride (Maybridge, Cornwall, UK) dissolved in dry acetonitrile (4 mL) and 6.25 mL (12.5 mmol) of 2 M trimethylsilyldiazomethane in hexanes (Aldrich, Milwaukee, Wis.) was stirred 1.75 h at room temperature and the mixture was cooled on an ice bath for 5 min. To this, 30% hydrogen bromide in acetic acid (2 mL, 10 mmol) was added dropwise over 10 min. This was stirred an additional 20 minutes on an ice bath. Evaporation of the solvents gave 1-[5-(tert-butyl)-2-methyl(3-furyl)]-2-bromoethan-1-one (1 g, 77%) as a brown oil. 1H-NMR (DMSO-d6; 300 MHz) δ6.50 (s, 1H), 4.57(s, 2H), 2.52 (s, 1H), 1.24 (s, 9H). Mass spectrum (LCA, m/z): Calcd. for C11H15O2Br, 259.1 and 261.1 (M+H), found 259.1 and 261.1.

후처리

  1. temperaturethe mixture was cooled on an ice bath for 5 min
  2. customEvaporation of the solvents

출처 및 근거

ORD 기록
ord-175a621a15c04ba6b0cead3d192e5b80
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492403B1

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