Acetyl chloride → HCID 20230255, compound

HRID 2290780Notes

Reaction equation

HRID 2290780 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:5]([C:7]1[O:11][N:10]=[C:9]([CH2:12][CH2:13][OH:14])[N:8]=1)[CH3:6].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C1COCC1>[C:31]([O:14][CH2:13][CH2:12][C:9]1[N:8]=[C:7]([CH:5]([CH3:6])[C:4]2[CH:15]=[CH:16][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:2]([F:1])[CH:3]=2)[O:11][N:10]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20230259HCID 20230259, compound

Product 1

HCID 20230255HCID 20230255, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.56 g of 5-(3-fluoro-4-phenyl-α-methylbenzyl)-3-(2-hydroxyethyl)-1,2,4-oxadiazole in 40 ml of dry THF were successively added dropwise 0.56 g of triethylamine and 0.43 g of acetyl chloride with ice-cooling. After stirring for 4 hours at room temperature, the reaction mixture was poured into ice-water and extracted with benzene. The organic phase was washed with sodium bicarbonate solution, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel using chloroform to give 1.57 g of 3-(2-acetoxyethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as a colorless oil, nD23 1.5564.

Workup

  1. temperaturecooling
  2. extractionextracted with benzene
  3. washThe organic phase was washed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-d88411c6f0a14580af098869ed8cc9c2
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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