HCID 22500660, compound → HCID 22500672, compound

HRID 1815435Notes

Reaction equation

HRID 1815435 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:17][CH2:18][C:19]([CH2:24]Cl)([CH3:23])[CH2:20][C:21]#[N:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)C>[CH2:1]([C:21]1[CH2:20][C:19]([CH2:18][O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:24])[CH2:23][N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22500660HCID 22500660, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 22500672HCID 22500672, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
100 °C

Procedure

A benzylmagnesium chloride solution in ether (224 ml, 1 M, 0.224 mol) is heated to 30° C. and a solution of 4-benzyloxy-3-chloromethyl-3-methylbutyronitrile (75%, 40 g, 0.126 mol) in diethyl ether (140 ml) is slowly added dropwise (30 min.). The suspension formed is kept at reflux by warming after complete addition. After 2 h, the ether (310 ml) is distilled off (45 min.) and then replaced by toluene abs. (210 ml). The yellow toluene suspension is heated to 100° C. and then stirred at this temperature for 2 h. The batch, which is cooled to room temperature, is treated with dil. HCl (10% strength, 100 ml) and stirred until, in addition to the aqueous and the toluene phase, a third, oily phase separates. The oil phase and water phase are separated off, and the toluene phase is extracted 2 times in a separating funnel with dil. HCl (100 ml). The oil phase combined with the HCl phases is washed with toluene (50 ml) and then adjusted to pH 8-9 with NaOH (32%). After stirring for 30 min., the separated oily base fraction is taken up with diethyl ether, and the alkaline water phase is extracted a further 3 times with ether (450 ml). The collected ether extracts are dried over Na2SO4 sicc. and concentrated. A red-brown oily residue of 39.64 g (96% of theory, 78% according to gc) remains.

Workup

  1. customThe suspension formed
  2. temperatureat reflux
  3. temperatureby warming
  4. additionafter complete addition
  5. distillationthe ether (310 ml) is distilled off (45 min.)
  6. temperatureThe batch, which is cooled to room temperature
  7. additionis treated with dil. HCl (10% strength, 100 ml)
  8. stirringstirred until,
  9. additionin addition to the aqueous and the toluene phase
  10. customThe oil phase and water phase are separated off
  11. extractionthe toluene phase is extracted 2 times in a separating funnel with dil. HCl (100 ml)
  12. washis washed with toluene (50 ml)
  13. stirringAfter stirring for 30 min.
  14. extractionthe alkaline water phase is extracted a further 3 times with ether (450 ml)
  15. dry with materialThe collected ether extracts are dried over Na2SO4 sicc
  16. concentrationand concentrated

Sources & evidence

ORD record
ord-e90a275fc68c44758c679350b0b5878e
Source dataset
uspto-grants-2005_04
Patent number
US06878738B1

Reaction notes

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