Triethylamine → HCID 658603, compound

HRID 2070988Notes

Reaction equation

HRID 2070988 reaction equation
Cl.[NH2:2][OH:3].CCN(CC)CC.[C:11]([C:15]1[C:16]([OH:23])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([CH3:14])([CH3:13])[CH3:12]>CC#N>[C:11]([C:15]1[C:16]([OH:23])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[N:2][OH:3])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 658603HCID 658603, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of hydroxylamine hydrochloride (437 mg, 6.3 mmol) in CH3CN at 0° C. was added Et3N and 3-tert-butyl-2-hydroxybenzaldehyde (1.02 g, 5.7 mmol). The reaction mixture was warmed up to room temperature and stirred for 24 h. The solvent was removed and the residue was dissolved in EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide 3-tert-butyl-2-hydroxybenzaldehyde oxime (1.01 g, 92%) as a pale yellow solid.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eee21e5ee85942b8aaf56d8646253965
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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