Hydrochloric Acid → HCID 21107245, compound

HRID 2377484Notes

Reaction equation

HRID 2377484 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([O:17]C)[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3(C)C)[CH2:3][CH2:2]1.[C-]#N.[Na+].C#N.Cl>CS(C)=O.CCCCCC.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([OH:17])[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][CH2:9]3)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 8929Sodium CyanideHCID 21107247HCID 21107247, compound2×

Product 1

HCID 21107245HCID 21107245, compoundYield 88.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-cyclopropyl-6-methoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 156, 1.5 g, 6.14 mmol) and sodium cyanide (2 g, 40.8 mmol) in anhydrous dimethylsulfoxide (25 mL) was heated at 230° C. overnight under argon. The reaction mixture was then cooled to ambient temperature, poured into ice and acidified (Caution! Hydrogen cyanide evolution!) with dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated to afford a dark brown oil. Flash column chromatography on silica gel (230-400 mesh) using 25% ethyl acetate in hexane as the eluent afforded the title compound as a solid (1.1 g, 78%).

Workup

  1. additionpoured into ice
  2. extractionextracted with ethyl acetate (×2)
  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 brown oil

Sources & evidence

ORD record
ord-25d90d8bae934fdb80d1a134a8265a28
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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