Water → 3,3-Dimethyl-4-(methyloxy)-2,3-dihydro-1-benzofuran

HRID 527542ノート

反応式

HRID 527542 の反応式
I[C:2]1[C:7]([O:8][CH2:9][C:10]([CH3:12])=[CH2:11])=[CH:6][CH:5]=[CH:4][C:3]=1[O:13][CH3:14].CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC.O>C1(C)C=CC=CC=1>[CH3:11][C:10]1([CH3:12])[C:2]2[C:3]([O:13][CH3:14])=[CH:4][CH:5]=[CH:6][C:7]=2[O:8][CH2:9]1

参加物

6

反応物 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 679668282-Iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzene2 回

生成物 1

HCID 575170913,3-Dimethyl-4-(methyloxy)-2,3-dihydro-1-benzofuran収率 75.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 2-iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzene (Intermediate 48, 6.08 g) in toluene (50 ml, SCRC) were added AIBN (3.61 g, 21.99 mmol, SCRC) and tributylstannane (11.60 g, 40.0 mmol, Aldrich). The reaction mixture was heated at reflux for 3 hours and then cooled to room temperature. Water (100 ml) was added and the mixture was extracted with ethyl acetate (3 times 200 ml, SCRC). The combined organic layers were dried, evaporated and purified by silica gel chromatography with as eluents EtOAc/PE (1/50) to afford the title compound as a yellow liquid (2.7 g).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate (3 times 200 ml, SCRC)
  4. customThe combined organic layers were dried
  5. customevaporated
  6. custompurified by silica gel chromatography with as eluents EtOAc/PE (1/50)

出典と根拠

ORDレコード
ord-2d3a03b2b4614ed8b440cbedcda1d0ee
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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