Sodium Cyanide → 5-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

HRID 2252251Notes

Reaction equation

HRID 2252251 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[C-]#N.[Na+]>CS(C)=O.O>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-oneYield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5,6-Dimethoxy-1-indanone (1 g, 5.20 mmol) and NaCN (2.55 g, 52 mmol) were combined in DMSO (10 mL). The reaction was stirred at 100° C. for two days, cooled, diluted with water and extracted with dichloromethane. The aqueous solution was acidified with concentrated HCl, and extracted with dichloromethane. The organic layer was dried over MgSO4 and evaporated to give the title compound (500 mg). MS (DCI/NH3) m/z: 178.99 (M+H)+. 1H NMR (500 MHz, CD2Cl2) δ ppm 2.59 (t, J=5.62 Hz, 2H) 3.01 (t, J=5.62 Hz, 2H) 3.93 (s, 3H) 6.33 (s, 1H) 6.95 (s, 1H) 7.17 (s, 1H).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-9da70f3e45174bd2a9e2cc83bc9a4fe0
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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