Diisobutylaluminum hydride → HCID 22397538, compound

HRID 1070695Notes

Reaction equation

HRID 1070695 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](/[CH:12]=[CH:13]/[C:14](OCC)=[O:15])=[CH:5]2.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](/[CH:12]=[CH:13]/[CH2:14][OH:15])=[CH:5]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 10755449HCID 10755449, compound

Product 1

HCID 22397538HCID 22397538, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (E)-3-(5,6-dichloroindol-2-yl)-2-propenoate (28 g, 98.5 mmol) in dry THF (500 ml) stirred under argon at −20° DIBAL (1M solution in hexane, 200 mmol) was added dropwise while keeping the temperature below −20°. The stirring was continued for one hour, then the reaction was quenched with water (70 m). After warming to RT diethyl ether (350 m) was added and the suspension was filtered on a Celite pad. The pad was washed with diethyl ether (3×100 ml), then the pooled organic phase was dried (MgSO4) and evaporated to give 23.85 g of the title compound (98.5 mmol, yield 100%) that was used as such in the next step.

Workup

  1. additionwas added dropwise
  2. customthe temperature below −20°
  3. customthe reaction was quenched with water (70 m)
  4. additionwas added
  5. filtrationthe suspension was filtered on a Celite pad
  6. washThe pad was washed with diethyl ether (3×100 ml)
  7. dry with materialthe pooled organic phase was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-395f9923be12470a94421e2f16be3307
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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