Diisobutylaluminum hydride → (1H-indol-5-yl)methanol

HRID 569739

Reaction equation

HRID 569739 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](OC)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C[AlH]CC(C)C)C>CCOCC>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 2773458(1H-indol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

96 g (0.548 mole) of 6b are treated analogously to Example 1a in 1,800 ml of ether and 1,391 ml (1.67 moles) of DIBAL (1.2 molar in toluene). After chromatography on silica gel with gradient elution with petroleum ether/ethyl acetate (3:1) and petroleum ether/ethyl acetate (1:1), 39.3 g (49%) of pure product are obtained. C9H9NO (147.2)

Workup

  1. washAfter chromatography on silica gel with gradient elution with petroleum ether/ethyl acetate (3:1) and petroleum ether/ethyl acetate (1:1), 39.3 g (49%) of pure product
  2. customare obtained

Sources & evidence

ORD record
ord-bc1b83dde3684cc4aa27d378a6abf204
Source dataset
uspto-grants-1988_03
Patent number
US04734407

Linked notes

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