Acetic Anhydride → HCID 86745842, compound

HRID 1196559Notes

Reaction equation

HRID 1196559 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]/[CH:21]=O.C(OC(=O)C)(=O)C.[F:30][C:31](Cl)(Cl)[C:32]([O:34][CH3:35])=[O:33]>O1CCCC1.C(OCC)C.[Zn]>[F:30]/[C:31](=[CH:21]\[CH:20]=[CH:19]\[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)/[C:32]([O:34][CH3:35])=[O:33]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 19898676HCID 19898676, compound

Product 1

HCID 86745842HCID 86745842, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Activated zinc powder (496 mg), powdered molecular sieve 4A (1.25 g) (ex. BDH) and cuprous chloride (84 mg) were suspended in anhydrous tetrahydrofuran (10 ml). (2E)-10-(2-Quinolinyloxy)dec-2-enal (1 g) was added followed by acetic anhydride (320 μl). The mixture was warmed to 50° under nitrogen and methyl fluorodichloroacetate (328 μl) was added. The mixture was warmed at 50-5° for 4 hours, additional zinc (0.2 g) was added and warming continued for 30 minutes. Upon cooling the reaction mixture was diluted with diethyl ether, filtered through celite and filtrate worked-up in standard fashion. Purification by column chromatography (silica; 4;1, hexane: ether) gave (2Z,4E) methyl 2-fluoro-12-(2-quinolinyloxy)dodeca-2,4-dienoate (0.26 g).

Workup

  1. temperatureThe mixture was warmed to 50° under nitrogen
  2. temperatureThe mixture was warmed at 50-5° for 4 hours
  3. temperaturewarming
  4. temperatureUpon cooling the reaction mixture
  5. filtrationfiltered through celite and filtrate
  6. customPurification by column chromatography (silica; 4;1, hexane: ether)

Sources & evidence

ORD record
ord-49cec63c31154511ad49a87aff0ed417
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

Loading…