Methyl iodide → 5Methyl-2-trimethylsilyl-4-furaldehyde

HRID 326358

反応式

HRID 326358 の反応式
[CH2:1]([Li])CCC.[CH3:6][Si:7]([CH3:16])([CH3:15])[C:8]1[O:9][CH:10]=[C:11]([CH:13]=[O:14])[CH:12]=1.IC>CCCCCC.O1CCCC1>[CH3:1][C:10]1[O:9][C:8]([Si:7]([CH3:16])([CH3:15])[CH3:6])=[CH:12][C:11]=1[CH:13]=[O:14]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418339Butyllithium2 回

生成物 1

HCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

n-Butyl lithium (a 1.6M solution in hexane; 2.04 ml, 3.28 mmol) was added dropwise to a solution of N,N'N'-trimethylethylenediamine (0.46 ml, 3.56 mmol) in tetrahydrofuran (7 ml) at -78 degrees under argon. After 15 minutes, a solution of 2-trimethylsilyl-4-furaldehyde (0.5 g, 2.98 mmol) in tetrahydrofuran (2 ml) was added, followed by n-butyl lithium (3.72 ml, 5.94 mmol) after 15 minutes. Iodomethane (1.12 ml, 17.9 mmol) was then added and the mixture was allowed to warm to room temperature gradually over 1/2 hour. The mixture was quenched with brine and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by flash chromatography using 10% ethyl ether/hexane. Fractions with Rf of about 0.22 on evaporation afforded the title methylfuran as a light yellow oil.

後処理

  1. customThe mixture was quenched with brine
  2. extractionextracted with ethyl ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by flash chromatography
  7. customFractions with Rf of about 0.22 on evaporation

出典と根拠

ORDレコード
ord-c7b1b100efeb4ab192a283dbeecb363c
出典データセット
uspto-grants-1993_12
特許番号
US05268387

関連ノート

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