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

HRID 2278300ノート

反応式

HRID 2278300 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 4, 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-f907047510b54049b790804f7d8bd713
出典データセット
uspto-grants-2015_09
特許番号
US09133175B2

反応ノート

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