Hydrochloric Acid → Tricyclo[8.2.1.03,8]trideca-3,5,7-trien-13-one

HRID 902436Notes

Reaction equation

HRID 902436 reaction equation
[Br-].[CH:2]12[C:14](=[N+]3CCCC3)[CH:11]([CH2:12][CH2:13]1)[CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:3]2.Cl.[OH2:21]>>[CH:2]12[C:14](=[O:21])[CH:11]([CH2:12][CH2:13]1)[CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:3]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 179861911-Tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-ylidene-pyrrolidinium bromide

Product 1

HCID 5260406Tricyclo[8.2.1.03,8]trideca-3,5,7-trien-13-one

Procedure

1-Tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-ylidene-pyrrolidinium bromide (225 mg, 0.70 mmol) was dissolved in water (5 mL) and 2 M aqueous HCl (5 mL) was added. The mixture was heated at reflux for 16 h, cooled and extracted into DCM. The organic extracts were concentrated to give tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one (130 mg) as a white crystalline solid. 1H NMR (CDCl3, 360 MHz) δ 7.19 (4 H, s, aromatic), 2.99-2.86 (4 H, m, benzylic), 2.61-2.57 (2 H, m, bridgehead H), 1.90-1.80 (2 H, m), 1.33-1.26 (2 H, m).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. extractionextracted into DCM
  5. concentrationThe organic extracts were concentrated

Sources & evidence

ORD record
ord-6fbccf322d6c487b9c20a4e3d22c19c0
Source dataset
uspto-grants-2008_04
Patent number
US07365196B2

Reaction notes

Loading…