Reaction #3097

Reaction equation

2,3-dihydrobenzofuran

α,α-dichloromethyl methyl ether

→

title compound

Yield 60.3%

2,3-Dihydrobenzofuran-5-carboxaldehyde

Yield 60.3%

Solvents

ether

CH2Cl2

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGstirred a further 30 minutes
2. 2
   Otherthe phases separated
3. 3
   ConcentrationThe organic phase was concentrated in vacuo
4. 4
   workup.DISTILLATIONthe residue purified by vacuum distillation

Procedure

To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2Cl2 (5 mL) maintaining the temperature at or below -35° C. The mixture was warmed to 0° C., stirred 1 hour, then poured into ice-water, and stirred a further 30 minutes. The mixture was diluted with ether, and the phases separated. The organic phase was concentrated in vacuo, and the residue purified by vacuum distillation to yield the title compound (1.25 g, 60%) as a colorless liquid. b.p. 119°-121° C. at 0.3 mm Hg.

Source