Hydrochloric Acid → 1-Cyano-6-methoxy-2-(2-oxo-3-phenylpropyl)-1,2,3,4-tetrahydronaphthalene

HRID 6399

Reaction equation

HRID 6399 reaction equation
[O:1]=[C:2]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]([CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[C:20]#[N:21])C(OC)=O.[OH-].[Li+].Cl>CO>[C:20]([CH:9]1[C:10]2[C:15](=[CH:14][C:13]([O:18][CH3:19])=[CH:12][CH:11]=2)[CH2:16][CH2:17][CH:8]1[CH2:3][C:2](=[O:1])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)#[N:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 19793281Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate

Product 1

HCID 197932351-Cyano-6-methoxy-2-(2-oxo-3-phenylpropyl)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate (4.63 g, 12 mmol), from Step 1, was dissolved in 100 mL of methanol and lithium hydroxide (77 mL of a 1.0M solution) was added. The reaction mixture was stirred overnight at ambient temperature and then acidified with 1N aqueous hydrochloric acid solution and extracted with diethyl ether. The ether extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The basic ether extract yielded 2.76 (70% yield) of the title compound; MS DCl--NH3M/Z: 337 (M+H)+.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. extractionThe basic ether extract

Sources & evidence

ORD record
ord-b7636b58c9434354a2f9df4dde371baa
Source dataset
uspto-grants-1993_09
Patent number
US05248677

Linked notes

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