Acetic Acid → HCID 12025898、化合物

HRID 2298626

反応式

HRID 2298626 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 12025898HCID 12025898、化合物収率 77%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-175a621a15c04ba6b0cead3d192e5b80
出典データセット
uspto-grants-2002_12
特許番号
US06492403B1

関連ノート

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