Acetyl chloride → HCID 15538830, compound

HRID 1901406Notes

Reaction equation

HRID 1901406 reaction equation
[CH:1]([C:4]([CH:15]([CH3:17])[CH3:16])=[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)[O:6][CH3:7])([CH3:3])[CH3:2].[C:18](Cl)(=[O:20])[CH3:19].C(OCC)(=O)C.CCCCCC>C(Cl)Cl.N1C=CC=CC=1>[C:18]([O:14][C:10]1[CH:9]=[C:8]([C:5]([O:6][CH3:7])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:15]([CH3:17])[CH3:16])[CH:13]=[CH:12][CH:11]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 15538829HCID 15538829, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 15538830HCID 15538830, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Alkene 1b (200 mg, 0.85 mmol) was dissolved in 20 mL of dry methylene chloride with 0.31mL of anhydrous pyridine. The flask was purged with argon and cooled in an ice bath. Acetyl chloride (0.115 g, 1.47 mmol) in 5 mL of dry methylene chloride was added dropwise over one hour. TLC analysis (silica, 20% ethyl acetate/hexane) indicated the reaction to be complete after 2.5 hours of stirring at 0° C. The solvents were evaporated and the residue dissolved in ethyl acetate. The solution was washed four times with water, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel, eluting with 10-20% ethyl acetate/hexane yielding 220 mg (93%) of 1c: 1H NMR (CDCl3) δ 7.37-6.99 (m, 4H), 3.19 (s, 3H), 2.47 (sept, 1H, J=6.9 Hz), 2.33 (sept, 1H, J=6.9 Hz), 2.29 (s, 3H), 1.24 (d, 6 H, J=6.9 Hz), 0.93 (d, 6 H, J=6.9 Hz); 13C NMR (CDCl3) δ 169.46, 150.62, 149.03, 139.02, 133.64, 128.95, 127.24, 122.89, 120.72, 56.50, 30.49, 26.98, 22.06, 21.25, 21.05.

Workup

  1. customThe flask was purged with argon
  2. temperaturecooled in an ice bath
  3. customthe reaction
  4. customThe solvents were evaporated
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washThe solution was washed four times with water
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with 10-20% ethyl acetate/hexane yielding 220 mg (93%) of 1c

Sources & evidence

ORD record
ord-34aed4c1976e4880948a938019539f58
Source dataset
uspto-grants-1996_11
Patent number
US05578253

Reaction notes

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