HCID 18665761, compound → HCID 18665760, compound

HRID 399252Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[C@H:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C@H:10]2[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])=[C:5]([O:37]COC)[CH:4]=1>C(O)C=C.Cl>[OH:37][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=2)[C@H:11]([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[C@H:10]1[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32]

Participants

Conditions

Temperature: 65 °C

Procedure

Allyl(1S,2R,3S)-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (1.7 g, 3.11 mmol) was dissolved in allyl alcohol (20 ml) and then 15 drops of conc. HCl was added. The resulting solution was stirred at 65° C. for 2 h. After removing the solvent the residue was partitioned between water and ethyl acetate. The organic layers were washed with water, 5% aqueous NaHCO3 and brine; then dried (MgSO4 anhyd.), filtered and evaporated to give an oil. The product was purified by column chromatography to provide the title compound as a pale yellow oil (1.26 g, 81%).

Workup

customAfter removing the solvent the residue
customwas partitioned between water and ethyl acetate
washThe organic layers were washed with water, 5% aqueous NaHCO3 and brine
dry with materialthen dried (MgSO4 anhyd.)
filtrationfiltered
customevaporated
customto give an oil
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-23bb847cf8c048c7a23cfe58a04c13e6
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05817693

Reaction notes

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