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

HRID 1484626노트

반응식

HRID 1484626 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 679668282-Iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzene2회

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b1ea6eb1f3724b83a713c5cf7de83b7b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422272B2

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