3,4-Dimethyl-5-phenyl-1,3-oxazolidine → HCID 86737596, compound

HRID 127636Notes

Reaction equation

HRID 127636 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].[CH3:25][N:26]1[CH:30]([CH3:31])[CH:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:28][CH2:27]1>>[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]([CH2:27][N:26]([CH:30]([CH3:31])[CH:29]([OH:28])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH3:25])[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 4346663,4-Dimethyl-5-phenyl-1,3-oxazolidineHCID 6442393(-)-Licarin A

Product 1

HCID 86737596HCID 86737596, compoundYield 29.5%

Procedure

20.0 g of trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran and 21.3 g of 3,4-dimethyl-5-phenyl-1,3-oxazolidine are held in 200 ml of absolute alcohol for 60 hours at 70° C. and subsequently the solvent and excess 3,4-dimethyl-5-phenyl-1,3-oxazolidine are removed, finally in vacuum. After purification by means of a chromatographic column there is obtained 9.1 g of N-(5-(trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenyl-benzofuran-2-yl)-2-hydroxy-3-methoxyphenylmethyl)-N-(1-hydroxy-1-phenyl-2-propyl)-N-methylamin, a yellow oil.

Workup

  1. customsubsequently the solvent and excess 3,4-dimethyl-5-phenyl-1,3-oxazolidine are removed, finally in vacuum
  2. customAfter purification by means of a chromatographic column

Sources & evidence

ORD record
ord-b43a3c11099e4803bfe19dca957216a0
Source dataset
uspto-grants-1981_03
Patent number
US04256764

Reaction notes

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