Water → Ethyl 2-(2-Butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionate

HRID 1633165

Reaction equation

HRID 1633165 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[OH2:10].[CH3:11][CH2:12][O:13][CH2:14][CH3:15]>>[CH3:2][CH:1]([CH:11]([C:1]([OH:3])([CH3:2])[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[C:12]([O:13][CH2:14][CH3:15])=[O:10])[CH2:4][CH3:9]

Participants

4

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 95893-Acetylpyridine

Product 1

HCID 54531343Ethyl 2-(2-Butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionateYield 74.5%

Procedure

To the above solution is added, with stirring, a solution of 3-acetylpyridine (24.2 grams, 0.2 mole) in 80 milliliters of ether. The mixture is stirred for 15 minutes at -78° C. and then allowed to warm up to room temperature (2 hours). Water is added and the ether layer is separated, washed with water, dried with magnesium sulfate and evaporated under reduced pressure to give an oil which weighs 48.0 grams. The oil is distilled in a Kugelrohr apparatus to yield 39.5 grams (74.5%) of the pure product, b.p. 95°-96° C. (air bath temperature) at 0.05 mm Hg.

Workup

  1. additionTo the above solution is added
  2. stirringThe mixture is stirred for 15 minutes at -78° C.
  3. customthe ether layer is separated
  4. washwashed with water
  5. dry with materialdried with magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give an oil which
  8. distillationThe oil is distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-d7909e99124947ee81f96d10be6fdbfc
Source dataset
uspto-grants-1984_10
Patent number
US04479003

Linked notes

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