Acetyl chloride → HCID 86586070, compound

HRID 2109589Notes

Reaction equation

HRID 2109589 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[C:8]([CH:19]=1)[O:9][CH2:10][CH:11]([OH:18])[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)([O-:3])=[O:2].[C:27](Cl)(=[O:29])[CH3:28]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]([F:26])([F:25])[C:21]([F:22])([F:23])[F:24])=[C:8]([CH:19]=1)[O:9][CH2:10][CH:11]([O:18][C:27](=[O:29])[CH3:28])[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 21959395HCID 21959395, compound

Product 1

HCID 86586070HCID 86586070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved 1-(5-nitro-2-pentafluoroethyl-phenoxy)-3-pyrrolidin-1-yl-propan-2-ol (3.5 g) in CH2Cl2 (15 ml), added TEA (2.55 ml) and cooled to 0° C. Acetyl chloride (781.3 μl) was added dropwise, forming a suspension. The mixture was warmed to RT and stirred for 1.5 h. Additional acetyl chloride (200 μl) was added and the mix was stirred for another h. The mixture was diluted with CH2Cl2 and washed with sat. NaHCO3. The organic layer was removed, washed with brine and back extracted with CH2Cl2. Dried the combined organic layers over Na2SO4, filtered and concentrated in vacuo. The residue was purified over silica gel column (5:94.5:0.5 MeOH: CH2Cl2:NH4OH) to provide acetic acid 2-(5-nitro-2-pentafluoroethyl-phenoxy)-1-pyrrolidin-1-ylmethyl-ethyl ester as a yellow brown oil.

Workup

  1. customforming a suspension
  2. temperatureThe mixture was warmed to RT
  3. stirringthe mix was stirred for another h
  4. washwashed with sat. NaHCO3
  5. customThe organic layer was removed
  6. washwashed with brine
  7. extractionback extracted with CH2Cl2
  8. dry with materialDried the combined organic layers over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified over silica gel column (5:94.5:0.5 MeOH: CH2Cl2:NH4OH)

Sources & evidence

ORD record
ord-d3124360cc0d43a6aff5c3cfbf8f77f8
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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