Sodium Hydroxide → HCID 19838107, compound

HRID 1381619Notes

Reaction equation

HRID 1381619 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=O)[CH2:15]/[CH:16]=[CH:17]/[CH2:18][C:19]([NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15]/[CH:16]=[CH:17]/[CH2:18][CH2:19][NH:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21276265HCID 21276265, compound

Product 1

HCID 19838107HCID 19838107, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (c) (6 g., 14.6 mmoles) and lithium aluminium hydride (1M solution in ether, 60 ml, 60 mmoles) in dry dichloromethane (200 ml) were heated at reflux under nitrogen for 5 hrs. The suspension was cooled and poured slowly into an ice-cold 10% aqueous solution of sodium hydroxide. The organic phase was separated, washed with brine and evaporated. Recrystallisation of the residue from 2-propanol afforded the sub-title compound (2.0 g) mp 270°-272°.

Workup

  1. temperatureat reflux under nitrogen for 5 hrs
  2. temperatureThe suspension was cooled
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customevaporated
  6. customRecrystallisation of the residue from 2-propanol

Sources & evidence

ORD record
ord-630c2030c7384bd5ac9e91f3a334dccc
Source dataset
uspto-grants-1989_02
Patent number
US04803225

Reaction notes

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