Colletochlorin B → HCID 11404648, compound

HRID 1437841Notes

Reaction equation

HRID 1437841 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]([CH3:19])[CH3:18])\[CH3:13])=[C:4]([OH:20])[C:3]=1[CH:21]=[O:22].[H][H]>[Pd].C(O)C>[Cl:8][C:7]1[C:2]([CH3:1])=[C:3]([C:4]([OH:20])=[C:5]([CH2:10][CH2:11][CH:12]([CH3:13])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]=1[OH:9])[CH:21]=[O:22]

Participants

5

Reactant 2

HCID 6439644Colletochlorin BHCID 178418361HCID 178418361, compound

Product 1

HCID 11404648HCID 11404648, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An ethanol solution (24.5 ml) of colletochlorin B (991 mg, 3.07 mmol) described in H. Saimoto et al., Bull. Chem. Soc. Jpn., 67, 1178 (1994) was stirred in the presence of 5% Pd/C (496 mg) at 0° C. in a hydrogen atmosphere for 4.5 hours. After the catalyst was separated by filtration with the use of Celite, the filtrate was concentrated to obtain a crude product (963 mg). This product was purified by silica gel column chromatography (hexane:diethyl ether=30:1) to obtain 3-chloro-4,6-dihydroxy-5-(3,7-dimethyloctyl)-2-methylbenzaldehyde (pale yellow solid 220 mg, yield 22%).

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 (963 mg)
  4. customThis product was purified by silica gel column chromatography (hexane:diethyl ether=30:1)

Sources & evidence

ORD record
ord-8cd76bd512944301ac10c6b2ac9e5d22
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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