Ethyl 5-ethoxyheptanoate → 5-Ethoxyheptanol

A solution of tetrhydrofuran (2000 ml) and lithium aluminum hydride (46 g, 1.21 moles) is cooled in a -60° C. dry ice/ethanol bath. The starting material prepared in Example 36, ethyl 5-ethoxyheptanoate (302 g, 1.49 moles) is diluted in tetrahydrofuran (300 ml) and added dropwise to the stirring reaction. After the addition is complete the reaction is warmed to room temperature and stirred for an additional hour. The solution is cooled in a -78° C. dry ice/ethanol bath and the excess hydride is destroyed by adding dropwise the following: water (46 ml), 15% sodium hydroxide solution (46 ml), and water (136 ml). The reaction is filtered and the solids washed several times with tetrahydrofuran (3×500 ml). The volume of the filtrate is reduced under vacuum and the residue dried over anhydrous magnesium sulfate. The remaining solvent is then removed leaving a clear, colorless oil suitably pure for the next reaction (238 g, 1.49 moles).

1. additionadded dropwise to the stirring reaction
2. additionAfter the addition
3. temperatureThe solution is cooled in a -78° C. dry ice/ethanol bath
4. customthe excess hydride is destroyed
5. additionby adding dropwise the following: water (46 ml), 15% sodium hydroxide solution (46 ml), and water (136 ml)
6. filtrationThe reaction is filtered
7. washthe solids washed several times with tetrahydrofuran (3×500 ml)
8. dry with materialthe residue dried over anhydrous magnesium sulfate
9. customThe remaining solvent is then removed
10. customleaving a clear, colorless oil
11. customsuitably pure for the next reaction (238 g, 1.49 moles)

ORD record

ord-03ed7a3060ad4d4585d83a0c5e1b3eab

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04855322