(-)-Licarin A → HCID 86737597, compound

HRID 127637Notes

Reaction equation

HRID 127637 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:28]1[CH2:32][CH2:31][O:30][CH2:29]1)[CH:26]=[CH2:27]>>[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]([CH2:29][N:28]([CH2:32][CH2:31][OH:30])[CH2:25][CH:26]=[CH2:27])[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

3

Reactant 2

HCID 6442393(-)-Licarin AHCID 13285775HCID 13285775, compound

Product 1

HCID 86737597HCID 86737597, compoundYield 53.5%

Procedure

20.0 g of trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofurane and 13.6 g of 3-allyl-1,3-oxazolidine are held in 240 ml of absolute alcohol for 48 hours at 70° C. and subsequently the solvent and excess 3-allyl-1,3-oxazolidine are removed in vacuum. After purification by means of a chromatographic column there is obtained 14.4 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-allylamine, a colourless oil.

Workup

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

Sources & evidence

ORD record
ord-9b0fcbe46c644ef4a95d70461d1ffe10
Source dataset
uspto-grants-1981_03
Patent number
US04256764

Reaction notes

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