Hydrochloric Acid → HCID 10446609, compound

HRID 392575Notes

Reaction equation

HRID 392575 reaction equation
[CH2:1]([C:5]12[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:10]([CH3:16])=[C:9]1[C:8]1[CH:17]=[CH:18][C:19]([O:21]COC)=[CH:20][C:7]=1[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl.C([O-])(O)=O.[Na+]>CO.ClCCl>[CH2:1]([C:5]12[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:10]([CH3:16])=[C:9]1[C:8]1[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:7]=1[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22664993HCID 22664993, compound

Product 1

HCID 10446609HCID 10446609, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 9a-butyl-2-(methoxymethoxy)-5-methyl-8,9,9a,10-tetrahydrobenzo[a]azulen-6(7H)-one(5 mg) in methanol (1 mL) was treated with aqueous 2N HCl (0.1 mL, 0.2 mmol). After stirring at 65° C. for two hours, the mixture was diluted with dichloromethane(2 mL), treated with solid NaHCO3, and purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 20% EtOAc in hexane. The UV visible product band was eluted with EtOAc and the eluant was evaporated under vacuum to provide 9a-butyl-2-hydroxy-5-methyl-8,9,9a,10-tetrahydrobenzo[a]azulen-6(7H)-one as a foam.

Workup

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

Sources & evidence

ORD record
ord-48a0356b55714635b7698641ab585fe7
Source dataset
uspto-grants-2004_10
Patent number
US06800785B1

Reaction notes

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