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

HRID 583704Notes

Reaction equation

HRID 583704 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 (1M 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-4e935d9421444d4aae4963d5d0c851b2
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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