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

HRID 1106195Notes

Reaction equation

HRID 1106195 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-3ac83655684a4301aef8207c0959ee15
Source dataset
uspto-grants-1982_01
Patent number
US04312368

Reaction notes

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