(-)-Licarin A → HCID 86737595, compound

HRID 127635Notes

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].[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]2[N:36]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:35][CH2:34][O:33]2)[CH:29]=[CH:30][CH:31]=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]([CH:32]([C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=4)[N:36]([CH2:35][CH2:34][OH:33])[CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=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

Reactant 2

HCID 6442393(-)-Licarin A

HCID 20285493HCID 20285493, compound

Product 1

HCID 86737595HCID 86737595, compoundYield 26.6%

Procedure

20.0 g of trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran and 32.8 g of 2-(3-chlorophenyl)-3-benzyl-1,3-oxazolidine are held in 260 ml of absolute alcohol for 60 hours at 70° C. and subsequently the solvent and excess of 2-(3-chlorophenyl)-3-benzyl-1,3-oxazolidine are removed, finally in vacuum. After purification by means of a chromatographic column there is obtained 9.8 g of N-(5-(trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenyl-benzofuran-2-yl)-2-hydroxy-3-methoxyphenyl-(3-chlorophenyl)-methyl)-N-(2-hydroxyethyl)-N-benzylamin, a bright yellow oil.

Workup

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

Sources & evidence

ORD record: ord-98f1c7b50f45401eb2fe9688d8bea0c1
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04256764

Reaction notes

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