Sodium borohydride → 4-Hydroxymethyl-2-triethylsilylfuran

HRID 273968

反応式

HRID 273968 の反応式
[BH4-].[Na+].[CH2:3]([Si:5]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]1[O:7][CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[CH3:4]>CO>[OH:12][CH2:11][C:9]1[CH:10]=[C:6]([Si:5]([CH2:13][CH3:14])([CH2:15][CH3:16])[CH2:3][CH3:4])[O:7][CH:8]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

生成物 1

HCID 150370354-Hydroxymethyl-2-triethylsilylfuran

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (353 mg, 0.93 mmol) was added portionwise to a solution of 2-triethylsilyl-4-furaldehyde (1.64 g, 7.79 mmol) in methanol (10 ml) at 0°. After 1 hour, most of the methanol was evaporated and the residue dissolved in a minimum amount of dilute hydrochloric acid. Extraction (ethyl acetate), drying (magnesium sulfate) and evaporation gave an oil, which was purified by flash chromatography on silica using 20% ethyl ether/hexane. Fractions with Rf of about 0.07 (10% ethyl ether/hexane) gave after evaporation the title alcohol as a colorless oil.

後処理

  1. custommost of the methanol was evaporated
  2. dissolutionthe residue dissolved in a minimum amount of dilute hydrochloric acid
  3. extractionExtraction (ethyl acetate)
  4. customdrying
  5. custom(magnesium sulfate) and evaporation
  6. customgave an oil, which
  7. customwas purified by flash chromatography on silica using 20% ethyl ether/hexane
  8. customFractions with Rf of about 0.07 (10% ethyl ether/hexane) gave
  9. customafter evaporation the title alcohol as a colorless oil

出典と根拠

ORDレコード
ord-30041682b03c4af08cb5bea47c723131
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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