Sodium Hydroxide → HCID 59267864, compound

HRID 1809408Notes

Reaction equation

HRID 1809408 reaction equation
[CH3:1][C:2]([CH3:20])([CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])[C:3](=O)[CH2:4][C:5]#[N:6].[OH-:21].[Na+].S(O)(O)(=O)=O.[NH2:28]O>O>[CH3:1][C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[O:21][N:28]=1)([CH3:20])[CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 59267907HCID 59267907, compound

Product 1

HCID 59267864HCID 59267864, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 15.32 g (51 mmol) of 4,4-dimethyl-3-oxo-5-triisopropylsilanyloxy-pentanenitrile and 8.44 g (211 mmol) of sodium hydroxide in water (150 mL) are added 8.87 g (54 mmol) of hydroxylamine sulfate. The reaction mixture is stirred at reflux for 28 h. After this time, the reaction mixture is cooled to room temperature and extracted with chloroform (3×150 mL). The organic layers are combined and washed with water (30 mL), dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure. The residual brown oil is purified by column chromatography (silica, eluent DCM, 0-1% methanol) to afford 2.82 g of 3-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-isoxazol-5-ylamine as a yellow solid. Yield 18%; m/z 313 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 0.98-1.15 (21H, m), 1.29 (6H, s), 3.68 (2H, s), 4.30 (2H, br. s.), 5.10 (1H, s)

Workup

  1. temperatureat reflux for 28 h
  2. extractionextracted with chloroform (3×150 mL)
  3. washwashed with water (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customThe residual brown oil is purified by column chromatography (silica, eluent DCM, 0-1% methanol)

Sources & evidence

ORD record
ord-41527f30b9c44c1fb9b25d96564b3839
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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