Pivaloyl chloride → HCID 15538832, compound

HRID 1901408Notes

Reaction equation

HRID 1901408 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:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>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:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 15538829HCID 15538829, compound

Product 1

HCID 15538832HCID 15538832, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Alkene 1b (2 g, 8.6 mmol) was dissolved in 50 mL of dry CH2Cl2 with 2.4 mL of anhydrous triethylamine. The flask was purged with argon and cooled in an ice bath. Pivaloyl chloride (1.6 g, 2 eq.) was added dropwise over one hour. The cooling bath was removed and stirring continued for 3 hours at room temperature. The solution was washed with aq. K2CO3 and then water, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel, eluting with 5% triethylamine in hexane yielding 1.95 g of dioxetane 1e: 1H NMR (CDCl3) δ 7.34-6.98 (m, 4H), 3.198 (s, 3H), 2.47 (sept, 1H), 2.33 (sept, 1H), 1.36 (s, 9H), 1.24 (d, 6 H, J=6.9 Hz), 0.92 (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. washThe solution was washed with aq. K2CO3
  5. dry with materialwater, dried over MgSO4
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with 5% triethylamine in hexane yielding 1.95 g of dioxetane 1e

Sources & evidence

ORD record
ord-ee43bbbbc1e54a24a9647d09e25186ce
Source dataset
uspto-grants-1996_11
Patent number
US05578253

Reaction notes

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