Diisobutylaluminum hydride → 2-(1H-indol-2-yl)ethanol

HRID 1599911Notes

Reaction equation

HRID 1599911 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][C:11](OCC)=[O:12].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 11106442Ethyl 2-(1H-indol-2-yl)acetate

Product 1

HCID 117884632-(1H-indol-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica 50% EtOAc/hexane) provided 4-2 as a brown oil.

Workup

  1. customquenched in sat. aqueous Na/K tartrate
  2. extractionThis solution was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb1fc554f030435f90c89467248bef55
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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