Ascofuranone → HCID 23134887, compound

HRID 1437842Notes

Reaction equation

HRID 1437842 reaction equation
[CH3:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[C:5]([CH2:10]/[CH:11]=[C:12](/[CH2:14][CH2:15]/[CH:16]=[C:17](/[C@H:19]2[O:24][C:23]([CH3:26])([CH3:25])[C:21](=[O:22])[CH2:20]2)\[CH3:18])\[CH3:13])=[C:4]([OH:27])[C:3]=1[CH:28]=[O:29].[H][H]>[Pd].C(O)C>[Cl:8][C:7]1[C:2]([CH3:1])=[C:3]([C:4]([OH:27])=[C:5]([CH2:10][CH2:11][CH:12]([CH3:13])[CH2:14][CH2:15][CH2:16][CH:17]([CH:19]2[CH2:20][C:21](=[O:22])[C:23]([CH3:25])([CH3:26])[O:24]2)[CH3:18])[C:6]=1[OH:9])[CH:28]=[O:29]

Participants

5

Reactant 2

HCID 6434242AscofuranoneHCID 178418361HCID 178418361, compound

Product 1

HCID 23134887HCID 23134887, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An ethanol (201 ml) solution of ascofuranone (1,058 mg, 2.52 mmlo) was stirred in the presence of 5% Pd/C (435 mg) in a hydrogen atmosphere at 0(C for three hours. After the catalyst was separated by filtration with the use of Celite, the filtrate was concentrated to obtain a crude product (1,178 mg). This product was purified by silica gel column chromatography (hexane:ethyl acetate═5:1) to obtain 3-chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-octyl]benzaldehyde (a diastereomeric mixture, yellow syrup 262 mg, yield 25%).

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 (1,178 mg)
  4. customThis product was purified by silica gel column chromatography (hexane:ethyl acetate═5:1)

Sources & evidence

ORD record
ord-5a6da47d821b44999f610e74ae848410
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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