(-)-Licarin A → HCID 86737598, compound

HRID 127638Notes

Reaction equation

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

Participants

Reactant 2

HCID 6442393(-)-Licarin A

HCID 125892683-Butyl-1,3-oxazolidine

Product 1

HCID 86737598HCID 86737598, compoundYield 56.6%

Procedure

20.0 g of trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofurane and 15.5 g of 3-butyl-1,3-oxazolidine are held in 180 ml of absolute alcohol for 36 hours at 70° C. and subsequently the solvent and excess 3-butyl-1,3-oxazolidine are removed in vacuum. After purification by means of a chromatographic column there is obtained 15.8 g of N-(5-(trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenyl-benzofuran-2-yl)-2-hydroxy-3-methoxyphenyl-methyl)-N-(2-hydroxyethyl)-N-butylamine, a colourless oil.

Workup

customsubsequently the solvent and excess 3-butyl-1,3-oxazolidine are removed in vacuum
customAfter purification by means of a chromatographic column

Sources & evidence

ORD record: ord-bad9cbfb56f84e0384d104e5174d3cc8
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04256764

Reaction notes

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