HCID 10093714, compound → HCID 10364829, compound

HRID 735389Notes

Reaction equation

HRID 735389 reaction equation
[CH3:1][C:2]1([CH3:32])[C:11]2[CH:10]=[C:9]([CH:12]([OH:24])[C:13]#[C:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[CH:8]=[CH:7][C:6]=2[C:5]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:4][CH2:3]1>CCCCC.ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1([CH3:32])[C:11]2[CH:10]=[C:9]([C:12](=[O:24])[C:13]#[C:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[CH:8]=[CH:7][C:6]=2[C:5]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)=[CH:4][CH2:3]1

Participants

5

Reactant 1

HCID 10093714HCID 10093714, compound

Product 1

HCID 10364829HCID 10364829, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Conditions

Temperature
37 °C

Procedure

0.1 g (0.237 mmol) of 4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-hydroxyprop-1-ynyl]benzoic acid (described in Example 15d) is dissolved in 2 ml of pentane and 2 ml of dichloromethane, 0.31 g (3.55 mmol) of manganese dioxide is then added and the medium is heated at 37° C. for 24 hours. The medium is filtered and concentrated, and the residue obtained is purified by chromatography (eluent: 85/15 heptane/ethyl acetate). A white solid is obtained (0.02 g; yield=20%).

Workup

  1. filtrationThe medium is filtered
  2. concentrationconcentrated
  3. customthe residue obtained
  4. customis purified by chromatography (eluent: 85/15 heptane/ethyl acetate)
  5. customA white solid is obtained (0.02 g; yield=20%)

Sources & evidence

ORD record
ord-5fc2b22847f6423f9fcb06a2983a675e
Source dataset
uspto-grants-2009_09
Patent number
US07592478B2

Reaction notes

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