Reaction #487568

Reaction equation

4-chloro-1H-pyrrolo[2,3-b]pyridine

[β-(trimethylsilyl)ethoxy]methyl chloride

N,N-dimethylformamide

sodium hydride

→

orange oil

Yield 112.5%

4-Chloro-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine

Yield 112.5%

Conditions

Workup

1. 1
   Otherpartitioned between ethyl acetate and water (×2)
2. 2
   Washthe organic layer was washed with sat. NaCl
3. 3
   OtherThe organic layer was then dried under vacuum

Procedure

To a 0° C. solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.50 g, 0.0033 mol) and [β-(trimethylsilyl)ethoxy]methyl chloride (0.75 mL, 0.0043 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was added sodium hydride (0.17 g, 0.0043 mol). The resulting mixture was stirred overnight and partitioned between ethyl acetate and water (×2), and the organic layer was washed with sat. NaCl. The organic layer was then dried under vacuum to produce 1.05 g of an orange oil which was chromatographed with 15% ethyl acetate/hex to give 830 mg of a colorless oil (89.6% yield).

Source