Diisobutylaluminumhydride → HCID 56839548, compound

HRID 1466782Notes

Reaction equation

HRID 1466782 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[CH3:28])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:21]([N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:11]([O:10][C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][CH:7]=2)=[C:12]1[CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 56839547HCID 56839547, compound

Product 1

HCID 56839548HCID 56839548, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-yloxy)-benzoic acid methyl ester (0.100 g, 0.25 mmol) was dissolved in THF (3 mL) and the solution was cooled to 0° C. Diisobutylaluminum hydride (0.750 mL, 1.0M in hexanes, 0.75 mmol) was added dropwise and the reaction was stirred for 20 minutes then an additional amount of diisobutylaluminum hydride (0.100 mL, 1.0M in hexanes, 0.10 mmol) was added. The reaction was allowed to stir for 20 minutes then quenched with aq. HCl (2 mL, 1M). The reaction was submitted to a standard workup procedure to give the title compound.

Workup

  1. stirringto stir for 20 minutes
  2. customthen quenched with aq. HCl (2 mL, 1M)

Sources & evidence

ORD record
ord-6afffbe90dd44a0ea0a9fc061e29b553
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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