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

반응식

[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

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 962Water

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

생성물 1

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

실험 절차

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).