Diisobutylaluminum hydride → {3-[2-(Methyloxy)ethyl]-1-naphthalenyl}methanol

HRID 337601Notes

Reaction equation

HRID 337601 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:15](OC)=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66896973Methyl 3-[2-(methyloxy)ethyl]-1-naphthalenecarboxylate

Product 1

HCID 66895342{3-[2-(Methyloxy)ethyl]-1-naphthalenyl}methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 3-[2-(methyloxy)ethyl]-1-naphthalenecarboxylate (1 eq.) from the previous step was taken up in toluene (0.1 M). To this solution was then added DIBAl-H (1.5 M toluene solution, 2.4 eq.) and the resulting solution was vigorously stirred at RT for 4 h. The reaction mixture thus obtained was quenched with 1 N aq. HCl and extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.

Workup

  1. customThe reaction mixture thus obtained
  2. customwas quenched with 1 N aq. HCl
  3. extractionextracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-349d526a99cd44dd8403205221475222
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…