2-Methyl-2-butanol → HCID 178467923, compound

HRID 989893Notes

Reaction equation

HRID 989893 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5]O.Cl.Cl[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[O-:15].C([O-])(O)=[O:17].[Na+].C(O)(CC)(C)C>>[OH:17][CH:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[O-:15]

Participants

5

Reactant 4

HCID 64052-Methyl-2-butanolHCID 258684-Amino-1-butanolHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 516892Sodium Bicarbonate

Product 1

HCID 178467923HCID 178467923, compoundYield 63.4%

Procedure

A mixture of 4-amino-1-butanol (2.0 mL, 21.7 mmole), 2-chloropyridine-N-oxide hydrochloride (3.00 g, g, 18.0 mmole), NaHCO3 (7.56 g, 90.0 mmole), and tert-amyl alcohol (22 mL) was heated at reflux. After 24 hr, the mixture was cooled and filtered, then the filtrate was concentrated under reduced pressure. Silica gel chromatography (10% MeOH/CHCl3) gave the title compound (2.08 g, 63%) as a yellow solid: MS (ES) m/e 183 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-725a001c5e3b47b2b930de63657ef8c2
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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