Chlorotrimethylsilane → 4-(1-Hydroxynonyl)-2-trimethylsilylfuran

HRID 654904ノート

反応式

HRID 654904 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Mg].Br[C:12]1[O:16][CH:15]=[C:14]([CH:17]=[O:18])[CH:13]=1.C([Li])(C)(C)C.Cl[Si:25]([CH3:28])([CH3:27])[CH3:26]>O1CCCC1.CCCCC>[OH:18][CH:17]([C:14]1[CH:13]=[C:12]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

参加物

8

反応物 5

HCID 6397ChlorotrimethylsilaneHCID 81401-BromooctaneHCID 5462224MagnesiumHCID 150370565-Bromofuran-3-carbaldehydeHCID 178418306HCID 178418306、化合物

生成物 1

HCID 157287174-(1-Hydroxynonyl)-2-trimethylsilylfuran

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 1-bromooctane (1.33 g, 6.9 mmol) and magnesium turnings (174 mg, 7.3 mmol) in tetrahydrofuran (8 ml) was refluxed under argon for 60 min. After cooling to 0°, a solution of 5-bromo-3-furaldehyde (1.21 g, 6.9 mmol) in THF (1 ml) was added and conditions maintained for 60 min. The mixture was further cooled to -78° and tert-butyl lithium (a 1.7M solution in pentane, 4.26 ml, 7.3 mmol) was added dropwise, followed by chlorotrimethylsilane (2.63 ml, 20.7 mmol) after 1h. Stirring was continued overnight while the cooling bath attained room temperature. The mixture was quenched with saturated aqueous ammonium chloride, diluted with water (15 ml) and extracted with ether. Evaporation of the dried (magnesium sulfate) extract gave a brown oil, which was subjected to flash chromatography on silica using 15% ethyl ether/petroleum ether. Fractions with Rf 0.2 on evaporation gave the captioned compound as a yellow oil.

後処理

  1. temperaturewas refluxed under argon for 60 min
  2. temperatureAfter cooling to 0°
  3. temperatureconditions maintained for 60 min
  4. temperatureThe mixture was further cooled to -78°
  5. customThe mixture was quenched with saturated aqueous ammonium chloride
  6. additiondiluted with water (15 ml)
  7. extractionextracted with ether
  8. customEvaporation of the
  9. dry with materialdried (magnesium sulfate)
  10. extractionextract
  11. customgave a brown oil, which
  12. customFractions with Rf 0.2 on evaporation

出典と根拠

ORDレコード
ord-a17000d9939544af872847d5d8b93c2a
出典データセット
uspto-grants-1992_07
特許番号
US05134128

反応ノート

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