Hydroxyamine hydrochloride → HCID 131720754, compound

HRID 1955693Notes

Reaction equation

HRID 1955693 reaction equation
[CH3:1][C:2]([C:5]([CH3:13])([CH2:10][CH:11]=[O:12])[C:6]([O:8][CH3:9])=O)([CH3:4])[CH3:3].[NH2:14][OH:15].Cl>N1C=CC=CC=1>[CH3:1][C:2]([C:5]([CH3:13])([CH2:10][CH:11]=[O:12])[C:6](=[N:14][OH:15])[O:8][CH3:9])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 10845239HCID 10845239, compound

Product 1

HCID 131720754HCID 131720754, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the aldehyde, methyl 2-(1,1-dimethylethyl)-2-methyl-4-oxobutanoate (2.05 g, 11 mmol) and H2NOH.HCl (1.15 g, 16.5 mmol) in dry pyridine (10 mL) was stirred at 60° C. for 4 h in a nitrogen atmosphere. After cooling the reaction mixture was poured into ice cold HCl (3N, 50 mL), and extracted with ether (3×40 mL). The combined ether extract was washed sequentially with 40 mL portions of saturated NaHCO3, water, and brine, and dried over MgSO4. The solvent was removed in vacuo to give 2.30 g of pale brown colored viscous liquid. Flash chromatography over silica gel (hexanes-EtOAc, 4:1) followed by bulb-to-bulb distillation (pot temp. 100°-105° C. (0.4 mmHg)) afforded the anti- and syn- oxime mixture (2.03 g, 92%) in the ratio of 58/42 as a colorless viscous liquid.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ether (3×40 mL)
  3. extractionThe combined ether extract
  4. washwas washed sequentially with 40 mL portions of saturated NaHCO3, water, and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f94095d0fc8d4eaeb9e34ad334c3fc8c
Source dataset
uspto-grants-1998_07
Patent number
US05776959

Reaction notes

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