Trifluoroacetic anhydride → HCID 59562802, compound

HRID 1801438Notes

Reaction equation

HRID 1801438 reaction equation
O[CH2:2][CH:3]([CH:6]([CH3:14])[CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[C:4]#[N:5].N12CCCN=C1CCCCC2.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH2:2]=[C:3]([CH:6]([CH3:14])[CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59562798HCID 59562798, compound

Product 1

HCID 59562802HCID 59562802, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 250 ml three-neck round-bottom flask which is dry and is purged with nitrogen is charged in succession with 19.7 g of the cyano alcohol (VII) (0.1 mol), 150 ml of anhydrous methylene chloride, and then 18.26 g (0.11 mol) of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The solution is cooled to 0° C. and then 22.05 g (0.105 mol) of trifluoroacetic anhydride are added dropwise, without 5° C. being exceeded in the mass. The resulting solution is stirred at ambient temperature for 16 hours and then hydrolyzed, dried, and concentrated. The residue is distilled under vacuum (6 torr) to give 16 g of unsaturated nitrile (VIII), which distills at 105-108° C. The yield is 89%.

Workup

  1. customA 250 ml three-neck round-bottom flask which is dry
  2. customis purged with nitrogen
  3. customdried
  4. concentrationconcentrated
  5. distillationThe residue is distilled under vacuum (6 torr)

Sources & evidence

ORD record
ord-e7459971a7a545b8a4242ebc5edc5317
Source dataset
uspto-grants-2013_01
Patent number
US08349790B2

Reaction notes

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