Deoxyhumulone → HCID 54356806, compound

HRID 567208Notes

Reaction equation

HRID 567208 reaction equation
[CH3:1][CH:2]([CH3:25])[CH2:3][C:4]([C:6]1[C:11]([OH:12])=[C:10]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[C:9]([OH:18])=[C:8]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C:7]=1[OH:24])=[O:5]>C(O)C.[C].[Pd]>[CH3:1][CH:2]([CH3:25])[CH2:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:9]([OH:18])=[C:10]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]=1[OH:12])=[O:5]

Participants

4

Reactant 1

HCID 6450808Deoxyhumulone

Product 1

HCID 54356806HCID 54356806, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 22.0 ml of ethanol, 1.50 g (4.34 mmol) of {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone (15) was dissolved. The solution was stirred with 924 mg (0.217 mmol, 5% equivalent) of 5% palladium carbon catalyst (water content up to 50%) under hydrogen atmosphere under ordinary pressure at room temperature for two hours. The solution was filtered and concentrated under a reduced pressure to form a brown oil. This oil was subjected to silica gel chromatography (using 100 g of Wako Gel C-200, eluted with hexane:ethyl acetate=10:1) to obtain 1.32 g (yield 86.6%) of the product (37) in the form of a colorless oily substance.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated under a reduced pressure
  3. customto form a brown oil
  4. washThis oil was subjected to silica gel chromatography (using 100 g of Wako Gel C-200, eluted with hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-4f688c016a1a41d08d7dd66f0c6d782b
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

Loading…