Hydrochloric Acid → HCID 11830380, compound

HRID 2181392Notes

Reaction equation

HRID 2181392 reaction equation
[OH:1][CH:2]([CH:7]([CH3:9])[CH3:8])[C:3](=[CH2:6])[C:4]#[N:5].N1C=CC=CC=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>O.C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[O:1][CH:2]([CH:7]([CH3:9])[CH3:8])[C:3]([C:4]#[N:5])=[CH2:6])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 112404803-Hydroxy-4-methyl-2-methylenepentanenitrile

Product 1

HCID 11830380HCID 11830380, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A nitrogen-purged 5 L, three-necked, round-bottom flask with overhead stirring is charged with 150 g (1.2 mol) of 3-hydroxy-4-methyl-2-methylenepentanenitrile, 1.0 L of methylene chloride, and 170 mL (2.1 mol) of pyridine. The solution is cooled at 10° C. to 15° C. in an ice bath. Using a 1 L graduated addition funnel, a mixture of 0.5 L of methylene chloride and 200 mL (2.1 mol) of ethyl chloroformate is added slowly while maintaining the reaction temperature at 20° C.±5° C. The reaction is stirred at 22° C.±3° C. for about two additional hours. The reaction solution is poured into a 6 L separatory funnel containing 200 mL (2.3 mol) of hydrochloric acid and 1.25 L of water. The lower organic layer is washed again with a solution of 60 mL (0.7 mol) of HCl and 0.5 L of water. The organic layer is dried over anhydrous magnesium sulfate (30 g), filtered, and concentrated by rotary evaporation to provide 226 g of carbonic acid 2-cyano-1-isopropyl-allyl ester ethyl ester as a yellow oil which may be used in the next step without further purification. Acetic acid 2-cyano-1-isopropyl-allyl ester (using acetyl chloride)

Workup

  1. customA nitrogen-purged 5 L
  2. temperatureThe solution is cooled at 10° C. to 15° C. in an ice bath
  3. additionaddition funnel
  4. additionis added slowly
  5. temperaturewhile maintaining the reaction temperature at 20° C.±5° C
  6. stirringThe reaction is stirred at 22° C.±3° C. for about two additional hours
  7. additionThe reaction solution is poured into a 6 L separatory funnel
  8. dry with materialThe organic layer is dried over anhydrous magnesium sulfate (30 g)
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6f696d9e1b8e48f19152e9ddb6b756c3
Source dataset
uspto-grants-2005_05
Patent number
US06891059B2

Reaction notes

Loading…