Hydrochloric Acid → HCID 9837536, compound

HRID 1582760Notes

Reaction equation

HRID 1582760 reaction equation
[CH3:1][CH:2]([C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:7][CH2:8][CH:9]=[O:10])[C:5]#[N:6])[CH3:3].P([O-])(O)(O)=[O:18].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].Cl>O.C(O)(C)(C)C>[C:5]([C:4]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][C:9]([OH:18])=[O:10])#[N:6]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 140258132-(1-Methylethyl)-5-oxo-2-phenylpentane nitrileHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 9837536HCID 9837536, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2-(1-Methylethyl)-5-oxo-2-phenylpentane nitrile, 6.00 g 27.9 mmol, was dissolved in a mixed solvent of water 55 ml/t-butyl alcohol 200 ml, and sodium dihydrogen phosphate 4.35 g 27.9 mmol and 2-methyl-2-butene 14.8 ml 139 mmol were further added thereto. Sodium chlorite 10.0 g 111 mmol in limited amounts was added thereto and stirred for 2 hours. The reaction mixture was ice-cooled and acidified by 2N hydrochloric acid. Then, it was extracted with ether, washed with dilute hydrochloric acid, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 4.10 g 17.7 mmol, 63.4%, was obtained as a white solid.

Workup

  1. additionwere further added
  2. temperaturecooled
  3. extractionThen, it was extracted with ether
  4. washwashed with dilute hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 4.10 g 17.7 mmol, 63.4%
  8. customwas obtained as a white solid

Sources & evidence

ORD record
ord-3713e5a1983840919374fc8fd6b89894
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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