3-Benzyloxazolidine → HCID 13145812, compound

HRID 127634Notes

Reaction equation

HRID 127634 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:32]1[CH2:36][CH2:35][O:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[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]([CH2:33][N:32]([CH2:36][CH2:35][OH:34])[CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[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

4

Reactant 2

HCID 3192583-BenzyloxazolidineHCID 6442393(-)-Licarin A

Product 1

HCID 13145812HCID 13145812, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.0 g of trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofurane and 20.0 g of 3-benyl-1,3-oxazolidine are held in 200 ml of absolute ethanol for 48 hours at 70° C. and subsequently solvent and excess 3-benzyl-1,3-oxazolidine are removed, finally in vacuum. After purification by means of a chromatographic column there is obtained 17.2 g of N-(5-(trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenyl-benzofuran-2-yl)-2-hydroxy-3-methoxy-phenylmethyl)-N-(2-hydroxyethyl)-N-benzylamine, a colourless oil, which solidifies in the manner of glass at oil pump vacuum.

Workup

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

Sources & evidence

ORD record
ord-2ea2efcca6ed479986e179b69d171454
Source dataset
uspto-grants-1981_03
Patent number
US04256764

Reaction notes

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