Hydrochloric Acid → HCID 21107254, compound

HRID 2377503Notes

Reaction equation

HRID 2377503 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([O:16]C)[CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][C:8]2([CH3:15])[CH3:14])[CH3:2].[C-]#N.[Na+].C#N.Cl>CS(C)=O.CCCCCC.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:16])[CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][C:8]2([CH3:15])[CH3:14])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 8929Sodium CyanideHCID 21107251HCID 21107251, compound2×

Product 1

HCID 21107254HCID 21107254, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-ethyl-4,4-dimethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (Intermediate 176, 1.1 g, 4.73 mmol) and sodium cyanide (1.6 g, 33 mmol) in anhydrous dimethylsulfoxide (20 mL) was heated at 210° C. overnight under argon. The reaction mixture was then cooled to ambient temperature, poured into ice and acidified (Caution! Hydrogen cyanide evolution!) using 10% hydrochloric acid and extracted with ethyl acetate. The combined organic extract was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated to afford a dark orange solid. Flash column chromatography on silica gel (230-400 mesh) using 10-20% ethyl acetate in hexane as the eluent afforded the title compound as a yellow solid (0.82 g, 82%).

Workup

  1. additionpoured into ice
  2. extractionextracted with ethyl acetate
  3. extractionThe combined organic extract
  4. washwas washed with brine (×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a dark orange solid

Sources & evidence

ORD record
ord-156d7ffc3bfa49909d04e5d3ab213196
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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