Water → HCID 14718883, compound

HRID 1085711Notes

Reaction equation

HRID 1085711 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[I-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C.[CH3:29][C:30]([C:33]1[N:38]=[CH:37][C:36]([C:39](=O)[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:35][N:34]=1)([CH3:32])[CH3:31].O>C(OCC)C.CCCCCC>[CH3:29][C:30]([C:33]1[N:38]=[CH:37][C:36]([C:39](=[C:2]([CH3:3])[CH3:1])[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:35][N:34]=1)([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 2723783Isopropyltriphenylphosphonium iodideHCID 14718729HCID 14718729, compoundHCID 178418339Butyllithium

Product 1

HCID 14718883HCID 14718883, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A 2.5 molar solution of n-butyl lithium in hexanes (5.5 cm3) was added in portions to a suspension of isopropyltriphenylphosphonium iodide (6 g) in dry diethyl ether, whilst the temperature was maintained between -10° and -20° C. After stirring for 1 hour at this temperature, a solution of ethyl 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-2-oxo-acetate (3 g) in dry diethyl ether (15 cm3) was added in portions. The stirred reaction mixture was allowed to warm to the ambient temperature, and allowed to stir for 16 hours. The reaction mixture was poured into water and extracted into ethyl acetate. The combined organic extracts were washed, dried over anhydrous magnesium sulphate, and concentrated by removal of the solvent under reduced pressure to give a dark brown oil, which was subjected to chromotography on silica gel, using hexane containing 10% ethyl acetate (by volume), as eluent to give ethyl 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3-methylbut-2-enoate (0.4 g) as a clear oil.

Workup

  1. temperaturewas maintained between -10° and -20° C
  2. customThe stirred reaction mixture
  3. stirringto stir for 16 hours
  4. extractionextracted into ethyl acetate
  5. washThe combined organic extracts were washed
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationconcentrated by removal of the solvent under reduced pressure
  8. customto give a dark brown oil, which

Sources & evidence

ORD record
ord-dfe967818d694618a3a1a35beee2deaa
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Reaction notes

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