Sodium Hydroxide → HCID 19838107, compound

HRID 2414022Notes

Reaction equation

HRID 2414022 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 (1 M 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-6e6d9b02ef2f450b9b821f58a5bae206
Source dataset
uspto-grants-1988_01
Patent number
US04720586

Reaction notes

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