Diisobutylaluminum hydride → HCID 6479255, compound

HRID 1741673Notes

Reaction equation

HRID 1741673 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13](OCC)=[O:14].CC(C[AlH]CC(C)C)C>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[CH2:13][OH:14]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 14360978HCID 14360978, compound

Product 1

HCID 6479255HCID 6479255, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-ethyl 3-(2-quinolinyl)-propenoate from Step 1 (2.13 g, 9.40 mmol) in THF (20 ml) at -78° C. was added dropwise a solution of DIBAL (1M in hexane) (3.5 eq). After 10 mins at -78° C., the reaction was quenched with 10 ml of 1M solution of Na+ /K+ tartrate and the mixture was allowed to warm to r.t. It was then processed in the usual manner with EtOAc and H2O. The residue was swished with EtOAc/hexane (1:2) to afford 1.36 g of the title alcohol.

Workup

  1. customthe reaction was quenched with 10 ml of 1M solution of Na+ /K+ tartrate

Sources & evidence

ORD record
ord-7971aaf6c3df4369a47e5bc099064584
Source dataset
uspto-grants-1994_08
Patent number
US05334597

Reaction notes

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