Tetrahydrofuran → 4-n-Butylidene-4,5,6,7-tetrahydrobenzo[b]furan

HRID 650595

反応式

HRID 650595 の反応式
O=[C:2]1[C:10]2[CH:9]=[CH:8][O:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:11]1[CH2:15]O[CH2:13][CH2:12]1.C([Mg]Br)CCC.[NH4+].[Cl-]>CCOC(C)=O>[CH:15](=[C:2]1[C:10]2[CH:9]=[CH:8][O:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)[CH2:11][CH2:12][CH3:13]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-oneHCID 178418682HCID 178418682、化合物

生成物 1

HCID 545187564-n-Butylidene-4,5,6,7-tetrahydrobenzo[b]furan

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 4-oxo-4,5,6,7-tetrahydrobenzo[b]furan (20.06 g) and THF (200 ml) was added dropwise 2M n-butylmagnesium bromide with ice-water cooling over 15 minutes. The mixture was stirred at r.t. overnight. The reaction mixture was poured into a mixture of a saturated aqueous solution of NH4Cl and AcOEt. The separated organic layer was washed with water and brine, and dried over MgSO4, and evaporated. The resulting oil was purified by chromatography on SiO2 (CHCl3 as eluent) to give 4-n-butylidene-4,5,6,7-tetrahydrobenzo[b]furan as a yellow oil (12.06 g).

後処理

  1. washThe separated organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe resulting oil was purified by chromatography on SiO2 (CHCl3 as eluent)

出典と根拠

ORDレコード
ord-274df34808e2475186d75710ee35a1fe
出典データセット
uspto-grants-2001_08
特許番号
US06274619B1

関連ノート

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