Sodium Hydroxide → HCID 86648131, compound

HRID 2388247Notes

Reaction equation

HRID 2388247 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[CH2:6]([O:8][C:9](=[O:18])[C:10](=[O:17])[CH:11]([CH3:16])[C:12](=O)[CH2:13][CH3:14])[CH3:7]>O>[CH2:6]([O:8][C:9](=[O:18])[C:10](=[O:17])[CH:11]([CH3:16])[C:12](=[N:4][OH:1])[CH2:13][CH3:14])[CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 3017239Ethyl 3-methyl-2,4-dioxohexanoate

Product 1

HCID 86648131HCID 86648131, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (1.58 g, 39.4 mmol) was dissolved in 8.5 mL of water. Hydroxylamine hydrochloride (2.74 g, 39.4 mmol) was added and the reaction mixture was stirred until complete dissolution was achieved. 3-Methyl-2,4-dioxo-hexanoic acid ethyl ester (6.37 g, 34.2 mmol) was added and the resulting mixture was stirred at ambient temperature for 16 h. The reaction mixture was extracted with EtOAc (3×50 mL) and the organic layers were combined, dried over MgSO4 and concentrated. The crude oil was purified by chromatography (0-40% EtOAc/hexanes) to give 3.7 g of the title compound. MS: (+) m/z 202.35 (M+1).

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 16 h
  2. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude oil was purified by chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-255dcc25df634218abac8988b00c4f94
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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