HCID 11267833, compound → HCID 23134877, compound

HRID 1437840Notes

Reaction equation

HRID 1437840 reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([C:7]([OH:22])=[C:8]([CH:11]([OH:21])[CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[C:9]=1[OH:10])[CH:5]=[O:6].[H][H]>[Pd].C(O)C>[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([C:7]([OH:22])=[C:8]([CH:11]([OH:21])[CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[C:9]=1[OH:10])[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 11267833HCID 11267833, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23134877HCID 23134877, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An ethanol solution (1.5 ml) of 3-chloro-5-(1-hydroxy-3,7-dimethyl-6-octenyl)-4,6-dihydroxy-2-methylbenzaldehyde (220) (196 mg, 0.57 mmol) was stirred at 0° C. in the presence of 5% Pd/C (50 mg) in a hydrogen atmosphere for 2 hours. After the catalyst was separated by filtration with the use of Celite, the filtrate was concentrated to obtain a crude product (188 mg). This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 3-chloro-5-(1-hydroxy-3,7-dimethyloctyl)-4,6-dihydroxy-2-methylbenzaldehyde (222, a diastereomeric mixture, red syrup 69 mg, crude yield 35%).

Workup

  1. customAfter the catalyst was separated by filtration with the use of Celite
  2. concentrationthe filtrate was concentrated
  3. customto obtain a crude product (188 mg)
  4. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-81ff34867deb4072b9e03638883fe2b5
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

Loading…