Reaction #985

Reaction equation

ester

4-[3-[1,3]-Dioxolan-2-yl-propyl)benzoic acid methyl ester

diisobutylaluminum hydride

→

alcohol

Yield 95.8%

[4-(3-[1,3]-Dioxan-2-yl-propyl)phenyl]methanol

Yield 95.8%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe reaction was quenched with saturated potassium sodium tartrate
2. 2
   Extractionextracted three times with ethyl acetate
3. 3
   DryingThe combined organic extracts were dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

To a solution of 2.85 g (11.4 mmol) of ester 169 in 25 mL of THF at 0° C. was added 4.4 mL (24.7 mmol) of diisobutylaluminum hydride and the resulting mixture was allowed to stir at 0° C. for 15 min. The reaction was quenched with saturated potassium sodium tartrate and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to yield 2.58 g of the crude alcohol 170 as an oil. 1H NMR consistent with the product.

Source