Benzoyl chloride → HCID 15538831, compound

HRID 1901407Notes

Reaction equation

HRID 1901407 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:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.C(N(CC)CC)C>[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:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 15538829HCID 15538829, compound

Product 1

HCID 15538831HCID 15538831, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Alkene 1b (4.5 g, 1.9 mmol) was dissolved in 50 mL of dry CH2Cl2 with 5.3 mL of anhydrous triethylamine. The flask was purged with argon and cooled in an ice bath. Benzoyl chloride (4.05 g, 2.9 mmol) was added dropwise. The cooling bath was removed and stirring continued for 1 hour at room temperature. The mixture was filtered and the solution was washed with water, dried over MgSO4 and evaporated. The residue was suspended in hexane, the solid filtered away and the solution evaporated. The residue was purified by column chromatography on silica gel, eluting with 1% ethyl acetate in hexane yielding 3.7 g of dioxetane 1d: 1H NMR (CDCl3) δ 8.25-7.05 (m, 9H), 3.25 (s, 1H), 2.54 (sept, 1H, J=6.9 Hz), 2.40 (sept, 1H, J=6.9 Hz), 2.29 (s, 3H), 1.26 (d, 6 H, J=6.9 Hz), 0.95 (d, 6 H, J=6.9 Hz).

Workup

  1. customThe flask was purged with argon
  2. temperaturecooled in an ice bath
  3. customThe cooling bath was removed
  4. filtrationThe mixture was filtered
  5. washthe solution was washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. filtrationthe solid filtered away
  9. customthe solution evaporated
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with 1% ethyl acetate in hexane yielding 3.7 g of dioxetane 1d

Sources & evidence

ORD record
ord-393c52fe03304b92a377210d53fc61b6
Source dataset
uspto-grants-1996_11
Patent number
US05578253

Reaction notes

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