Diphenyl Ether → 1-Allyl-1,3,3a,4,5,12a-hexahydro-7,13-dioxo-1,5-methano-furo[3,4-d]xanthene

HRID 734182Notes

Reaction equation

C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:23])[C:10]3[C:15]([O:16][C:17]=2[C:18]=1[O:19][CH2:20][CH:21]=[CH2:22])=[CH:14][CH:13]=[CH:12][CH:11]=3)C=C.[C:24]1(OC2C=CC=CC=2)[CH:29]=CC=C[CH:25]=1>>[CH2:29]([C:18]12[C:5](=[O:4])[CH:6]3[CH:7]=[C:8]4[C:17]1([CH:21]([CH2:22]3)[CH2:20][O:19]2)[O:16][C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:9]4=[O:23])[CH:24]=[CH2:25]

Participants

Reactant 2

HCID 7583Diphenyl Ether

HCID 161050373,4-Bis-allyloxyxanthen-9-one

Product 1

HCID 112668131-Allyl-1,3,3a,4,5,12a-hexahydro-7,13-dioxo-1,5-methano-furo[3,4-d]xantheneYield 12%

Procedure

A stirred solution of 3,4-bis-allyloxy-xanthen-9-one (236.4 mg, 0.767 mmol) and diphenyl ether (3.0 mL) was refluxed in an oil bath at 190° C. for 11 h. The solution was cooled to room temperature and product was purified twice by flash column chromatography (dichloromethane) to yield 28.0 mg (12%) of the title compound as a white solid. 1H NMR (CDCl3, 300 MHz): δ 7.95 (dd, J1=7.69 Hz, J2=1.65, 1H), 7.56 (ddd, J1=8.17 Hz, J2=7.07, J3=1.58, 1H), 7.34 (d, J=7.14Hz, 1H), 7.08 (m, 1H), 5.22 (m, 1H), 4.69 (m, 1H), 4.53 (m, 1H), 3.91 (d, J=7.97 Hz, 1H), 3.53 (ddd, J1=6.11 Hz, J2=3.43, J3=2.06, 1H), 2.82 (dd, J1=13.33 Hz, J2=5.35, 1H), 2.63 (m, 1H), 2.51 (dd, J1=13.60 Hz, J2=9.48, 1H), 1.90 (m, 1H), 1.78 (ddd, J1=12.22 Hz, J2=10.38, J3=2.39, 1H).

Workup

customproduct was purified twice by flash column chromatography (dichloromethane)

Sources & evidence

ORD record: ord-15fd558185f541c5b36c9be3ef750bb4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592143B2

Reaction notes

Loading…