HCID 22664992, compound → HCID 22664993, compound

HRID 2113685Notes

Reaction equation

HRID 2113685 reaction equation
[CH2:1]([C:5]12[CH2:14][CH2:13][CH2:12][CH:11]=[C:10]([CH3:15])[C:9]1(O)[C:8]1[CH:17]=[CH:18][C:19]([O:21][CH2:22][O:23][CH3:24])=[CH:20][C:7]=1[CH2:6]2)[CH2:2][CH2:3][CH3:4].[Cr](Cl)([O-])(=O)=[O:26].[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([C:5]12[CH2:14][CH2:13][CH2:12][C:11](=[O:26])[C:10]([CH3:15])=[C:9]1[C:8]1[CH:17]=[CH:18][C:19]([O:21][CH2:22][O:23][CH3:24])=[CH:20][C:7]=1[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 22664992HCID 22664992, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 22664993HCID 22664993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9a-butyl-2-(methoxymethoxy)-5-methyl-8,9,9a,10-tetrahydrobenzo[a]azulen-4b(7H)-ol (32 mg, 0.1 mmol) in dichloromethane (1 mL) was treated with pyridinium chlorochromate (PCC, 32 mg, 0.15 mmol). After stirring at room temperature for 5 hours, the mixture was treated with additional PCC (5 mg, 0.023 mmol). The mixture was concentrated and purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 10% EtOAc in hexane. The UV visible product band was eluted with EtOAc and the eluant was evaporated under vacuum to provide 9a-butyl-2-(methoxymethoxy)-5-methyl-8,9,9a,10-tetrahydrobenzo[a]azulen-6(7H)-one as an oil.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.)
  3. washThe UV visible product band was eluted with EtOAc
  4. customthe eluant was evaporated under vacuum

Sources & evidence

ORD record
ord-9b613ac00d014de89e58b6e571e800a8
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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