Sodium Hydroxide → HCID 22247174, compound

HRID 1815943Notes

Reaction equation

HRID 1815943 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:22]=[O:23])=[C:13]([N:15]([CH2:18][CH:19]([OH:21])[CH3:20])C=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:22]=[O:23])=[C:13]([NH:15][CH2:18][CH:19]([OH:21])[CH3:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22247178N-(5-Benzyloxy-2-formylphenyl)-N-(2-hydroxypropyl)-formamide

Product 1

HCID 22247174HCID 22247174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ice-cooled solution of the product from Step B (298 g, 0.95 mol) in THF (3 L) was treated with 1 M aqueous sodium hydroxide (1.95 L, 1.9 mol) keeping the temperature below 8° C. After the starting material was consumed, the mixture was diluted with brine and extracted twice with ethyl ether. The organic solution was washed with water until neutral and then with brine, dried over sodium sulfate, treated with charcoal and passed through silica (1 kg) with ether and with 1:1 ethyl acetate-hexane to yield, after concentration in vacuo, a yellow solid (207 g, 76%).

Workup

  1. customthe temperature below 8° C
  2. customAfter the starting material was consumed
  3. additionthe mixture was diluted with brine
  4. extractionextracted twice with ethyl ether
  5. washThe organic solution was washed with water until neutral and then with brine
  6. dry with materialdried over sodium sulfate
  7. additiontreated with charcoal
  8. customto yield
  9. concentrationafter concentration in vacuo

Sources & evidence

ORD record
ord-1734a58b96084e46b7cdbcc4e74eae4d
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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