Tetrahydrofuran → HCID 12449510, compound

HRID 1763590Notes

Reaction equation

HRID 1763590 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]#[N:11])=[CH:5][CH:4]=1.O1CCCC1.[OH-].[K+].[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH:28]=[CH2:29]>C(O)C>[C:10]([C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:4][CH:5]=1)([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH2:29][CH2:28][C:27]([O:31][CH2:32][CH3:33])=[O:30])#[N:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8821Ethyl Acrylate2×HCID 14797Potassium HydroxideHCID 12449500HCID 12449500, compound

Product 1

HCID 12449510HCID 12449510, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 52.3 g. of α-(α,α,α-trifluoro-p-tolyl)-4-morpholineacetonitrile in 500 ml. of dry tetrahydrofuran is stirred at ambient temperature while 1 ml. portions of 30% potassium hydroxide in ethanol and 25 ml. portions of ethyl acrylate is added every half hour until a total of 5 ml. of the base and 150 ml. of ethyl acrylate is added. After the addition, the mixture is stirred at ambient temperature for 48 hours. Following filtration, the filtrate is concentrated, dissolved in methylene chloride, passed through magnesol and recrystallized from methylene chloride/hexane to afford ethyl γ-cyano-γ(α,α,α-trifluoro-p-tolyl)-4-morpholinebutyrate as cream colored crystals, m.p. 96° -97° C.

Workup

  1. additionAfter the addition
  2. filtrationfiltration
  3. concentrationthe filtrate is concentrated
  4. dissolutiondissolved in methylene chloride
  5. customrecrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-556ce4f2e1c741ada993ba0bfd9ca199
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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