Diisobutylaluminum hydride → 2-(6-Chloropyridin-2-yl)ethanol

HRID 1599952Notes

Reaction equation

HRID 1599952 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9](OCC)=[O:10])[N:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][OH:10])[N:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 18928624Ethyl 2-(6-chloropyridin-2-yl)acetate

Product 1

HCID 189285562-(6-Chloropyridin-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 30-1 (1.34 g, 6.7 mmol) was dissolved in 10 mL CH2Cl2 at -78°, DIBAL (1 M in CH2Cl2, 17 mL, 17 mmol) was added, the mixture was warmed to RT for 15 min before quenching in a mixture of 25 mL saturated aqueous Na--K tartrate and 100 mL EtOAc. This mixture was shaken vigorously. The phases were allowed to separate, and the organic layer was washed with brine, dried (MgSO4), concentrated and chromatographed (silica, 40% EtOAc/hexane), providing 30-2 as a yellow oil.

Workup

  1. custombefore quenching in a mixture of 25 mL saturated aqueous Na--K tartrate and 100 mL EtOAc
  2. customto separate
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customchromatographed (silica, 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-aa976bd1eac34e858bf8d80a83df0db8
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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