Sodium Hydroxide → HCID 22247174, compound

HRID 2121862Notes

Reaction equation

HRID 2121862 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-054df37d290844e1b540be7e8c8bdcc9
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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