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

HRID 2278300Notes

Reaction equation

HRID 2278300 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 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).

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-f907047510b54049b790804f7d8bd713
Source dataset
uspto-grants-2015_09
Patent number
US09133175B2

Reaction notes

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