Sodium Hydroxide → HCID 19838107, compound

HRID 476685Notes

Reaction equation

HRID 476685 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-bd3e85bf91ea4534a8dfe47680aec5bc
Source dataset
uspto-grants-1989_12
Patent number
US04885313

Reaction notes

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