Triethylamine → Isopropyl (2Z)-3-hydroxy-2-cyano-4-ethyl-2-hexenoate

HRID 2262444Notes

Reaction equation

HRID 2262444 reaction equation
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[C:9]([CH2:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])#[N:10].C(N(CC)CC)C>C(Cl)Cl>[OH:5]/[C:4](/[CH:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[C:11](/[C:9]#[N:10])\[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25917Isopropyl cyanoacetateHCID 759542-Ethylbutyryl chloride

Product 1

HCID 54693160Isopropyl (2Z)-3-hydroxy-2-cyano-4-ethyl-2-hexenoateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

22.2 g (0.16 mol) of 2-ethylbutyryl chloride were added to a solution of 21 g (0.16 mol) of isopropyl cyanoacetate in CH2Cl2, and the reaction mixture was cooled to 0° C. At this temperature, with ice-cooling, 33.5 g (0.33 mol) of triethylamine were added dropwise, and the mixture was then stirred at 25° C. for 2 h. Following subsequent acidic hydrolysis, the organic phase was washed, dried and concentrated. Purification by customary methods gave 24.4 g of the title compound (68% of theory) as a colorless oil (b.p. 70-75° C./1.5 mbar).

Workup

  1. temperatureAt this temperature, with ice-cooling
  2. customacidic hydrolysis
  3. washthe organic phase was washed
  4. customdried
  5. concentrationconcentrated
  6. customPurification by customary methods

Sources & evidence

ORD record
ord-461234f4e4274a74b54408507a4eb786
Source dataset
uspto-grants-2010_12
Patent number
US07851411B2

Reaction notes

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