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

HRID 527542Notes

Reaction equation

HRID 527542 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2d3a03b2b4614ed8b440cbedcda1d0ee
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…