Hydroxyamine hydrochloride → HCID 57523584, compound

HRID 1879088Notes

Reaction equation

HRID 1879088 reaction equation
O[CH:2]=[C:3]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]([CH3:16])([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.Cl.[NH2:18]O>C(O)C.O>[CH3:16][C:5]1([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][C:3]2[CH:2]=[N:18][O:9][C:8]=2[CH:7]=[CH:6]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67113850HCID 67113850, compound

Product 1

HCID 57523584HCID 57523584, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 6-(hydroxymethylene)-4-methyl-4-((trimethylsilyl)ethynyl)-cyclohex-2-enone (147 mg, 0.63 mmol) in ethanol (15 mL) was added a solution of hydroxylamine hydrochloride (452 mg) in water (0.65 mL). The mixture was heated under reflux for 1 h. To the mixture was added water (50 mL). The aqueous mixture was extracted with methylene chloride/ether (1:2, 50 mL×3). The extract was washed with saturated aqueous sodium bicarbonate solution (50 mL×1) and brine (50 mL×1), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give 9 as a crystalline solid (145 mg, quantitative yield): 1H NMR (CDCl3) δ 8.06 (1H, s), 6.47 (1H, d, J=9.9 Hz), 6.03 (1H, d, J=9.9 Hz), 3.07 (1H, d, J=16.1 Hz), 2.77 (1H, d, J=16.1 Hz), 1.37 (3H, s), 0.14 (9H, s). This material was used without further purification for the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 h
  3. extractionThe aqueous mixture was extracted with methylene chloride/ether (1:2, 50 mL×3)
  4. washThe extract was washed with saturated aqueous sodium bicarbonate solution (50 mL×1) and brine (50 mL×1)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-68c9888d062240b5a0e90a6fa1db5fd2
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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