Lithium hydroxide, monohydrate → HCID 22633671, compound

HRID 2416988Notes

Reaction equation

HRID 2416988 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:21])([CH3:20])[CH2:7][C:8](C=O)([CH2:13][CH2:14][C:15](=[O:17])[CH3:16])[C:9]2=O)=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[C:6]([CH3:20])([CH3:21])[CH2:7][C:8]1[CH2:13][CH2:14][C:15](=[O:17])[CH2:16][C:9]2=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22633674HCID 22633674, compound

Product 1

HCID 22633671HCID 22633671, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 7-bromo-4,4-dimethyl-2-formyl-2-(3-oxo-butyl)-1-oxo-1,2,3,4-tetrahydronaphthalene (1.71 g, 4.87 mmol) in methanol (170 ml) was treated with a solution of lithium hydroxide hydrate (0.854 g, 20.35 mmol) in water (85 ml) the reaction was stirred at room temperature for 45 minutes and then the temperature was raised to 50° C. and the mixture was stirred for another 2 hours. The reaction was quenched with water and adjusted to pH 5 with 4M hydrochloric acid. The aqueous phases were extracted with ethylacetate (3×) and the combined organic phases were washed with water and dried over anhydrous magnesium sulfate. The residue was purified by silica gel chromatography (hexane/ethylacetate 95:5 to 90:10) to give the title material (0.631 g, 42%) along with 6-bromo-9,9-dimethyl-3-oxo-1,2,3,4,9,10-hexahydrophenanthrene (0.371 g, 25%).

Workup

  1. temperaturethe temperature was raised to 50° C.
  2. stirringthe mixture was stirred for another 2 hours
  3. customThe reaction was quenched with water
  4. extractionThe aqueous phases were extracted with ethylacetate (3×)
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue was purified by silica gel chromatography (hexane/ethylacetate 95:5 to 90:10)

Sources & evidence

ORD record
ord-7c66cd82225544ba97ab971f2061051a
Source dataset
uspto-grants-2004_11
Patent number
US06825233B2

Reaction notes

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