Acetic Anhydride → 5-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

HRID 273951

反応式

HRID 273951 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Mg].[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:18][C:17]=1[CH:25]=[O:26].[C:27](OC(=O)C)(=[O:29])[CH3:28]>O1CCCC1>[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:22])([CH3:24])[CH3:23])=[CH:18][C:17]=1[CH:25]([O:26][C:27](=[O:29])[CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 89191-BromododecaneHCID 5462224MagnesiumHCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

生成物 1

HCID 194331855-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 1-bromododecane (261 mg, 0.11 mmol) and magnesium turnings (27 mg, 0.11 mmol) in tetrahydrofuran (7 ml) was refluxed under argon for 1 hour. After cooling to room temperature, a solution of 5-methyl-2-trimethylsilyl-4-furaldehyde (158.6 mg, 0.87 mmol) in tetrahydrofuran (1 ml) was added, followed by acetic anhydride (0.25 ml, 2.6 mmol) after 1 hour. Stirring was continued at room temperature overnight and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a light yellow oil.

後処理

  1. temperaturewas refluxed under argon for 1 hour
  2. customthe mixture was quenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane)

出典と根拠

ORDレコード
ord-772e3bb2c85549f186a2d2451c552926
出典データセット
uspto-grants-1995_02
特許番号
US05387606

関連ノート

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