Reaction #43628

Reaction equation

butyl 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]propanoate

LiAlH4

water

→

product

Yield 102.3%

3-[4-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-1-propanol

Yield 102.3%

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGto stir for 1 h
2. 2
   Filtrationbefore being filtered
3. 3
   Otherevaporated

Procedure

A solution of butyl 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]propanoate (4.76 g, 12.49 mmol) in THF (120 ml) was treated with LiAlH4 soln (1M in THF, 12.49 ml, 12.49 mmol) at −78° C. The reaction mixture was allowed warm to −20° C. and after stirring at −20° C. for 15 min, the mixture was treated with water (9 ml) and allowed to stir for 1 h before being filtered and evaporated to give a slightly impure product (3.98 g, 102%).

Source