Sodium Cyanide → 2-Cyanomethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

HRID 862970Notes

Reaction equation

HRID 862970 reaction equation
CS(O[CH2:6][CH:7]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH2:25][O:26][CH3:27])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:28][CH2:29][CH2:30][CH3:31])[CH:13]=2)[CH:8]1[C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)(=O)=O.[C-:41]#[N:42].[Na+]>CN(C=O)C>[C:41]([CH2:6][CH:7]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH2:25][O:26][CH3:27])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:28][CH2:29][CH2:30][CH3:31])[CH:13]=2)[CH:8]1[C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)#[N:42]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 21714794(1RS,2RS,3RS)-2-Methanesulfonyloxymethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

Product 1

HCID 867521282-Cyanomethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1RS,2RS,3RS)-2-Methanesulfonyloxymethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (1.5 g, 2.96 mmol) was stirred in DMF (10 ml) under argon with NaCN (1.45 g, 29.6 mmol) at 60° C. for 20 h then cooled and partitioned between EtOAc and 3N HCl. The organic extract was washed with H2O, saturated NaHCO3 solution, H2O, then brine, dried (Na2SO4) and solvent removed in vacuo to afford the title compound as an oil (1.27 g, 86%).

Workup

  1. temperaturethen cooled
  2. custompartitioned between EtOAc and 3N HCl
  3. extractionThe organic extract
  4. washwas washed with H2O, saturated NaHCO3 solution, H2O
  5. dry with materialbrine, dried (Na2SO4) and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-93eac9b6dee8462fbdb43bf90f7f441e
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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