CHEBI:5834 → HYPERFORIN

HRID 1097123Notes

Reaction equation

HRID 1097123 reaction equation
[CH3:1][CH:2]([C:4]([C@@:6]12[C@@:16]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])([CH3:17])[C@@H:15]([CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH2:14][C@@:11]([CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])([C:12]1=[O:13])[C:10]([OH:34])=[C:9]([CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])[C:7]2=[O:8])=[O:5])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:3][CH:2]([C:4]([C:6]12[C:16]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:22])[CH3:23])([CH3:17])[CH:15]([CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])[CH2:14][C:11]([CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])([C:12]1=[O:13])[C:10]([OH:34])=[C:9]([CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])[C:7]2=[O:8])=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 441298CHEBI:5834HCID 21226445Aluminium lithium hydride

Product 1

HCID 3662HYPERFORIN

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g of hyperforin (M. W. =536,01) are dissolved in 20 ml of THF under magnetic stirring; the solution is added with LiAlH4 in strong excess (1 g, 0.026 mol, M. W.=38). The progress of the reaction is monitored by TLC (eluent petroleum ether/EtOAc 9:1). After ten minutes the reaction is completed.

Workup

  1. waitAfter ten minutes the reaction is completed

Sources & evidence

ORD record
ord-5c41414fca4e4c35a84c067f7dcd1a5c
Source dataset
uspto-grants-2012_03
Patent number
USRE043280E1

Reaction notes

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