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

HRID 862971Notes

Reaction equation

HRID 862971 reaction equation
[C:1]([CH2:3][CH:4]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21]COC)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:25][CH2:26][CH2:27][CH3:28])[CH:10]=2)[CH:5]1[C:29]1[CH:34]=[CH:33][C:32]2[O:35][CH2:36][O:37][C:31]=2[CH:30]=1)#[N:2]>CCO.Cl>[C:1]([CH2:3][CH:4]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[OH:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:25][CH2:26][CH2:27][CH3:28])[CH:10]=2)[CH:5]1[C:29]1[CH:34]=[CH:33][C:32]2[O:35][CH2:36][O:37][C:31]=2[CH:30]=1)#[N:2]

Participants

4

Reactant 1

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

Product 1

HCID 867521292-Cyanomethyl-3-(2-hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

1RS,2RS,3RS)-2-Cyanomethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (300 mg, 0.60 mmol) was dissolved in EtOH (4 ml) with concentrated HCl (0.1 ml) then refluxed for 1 h. the mixture was cooled then 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 a solid foam (250 mg, 91%).

Workup

  1. temperaturethen refluxed for 1 h. the mixture
  2. temperaturewas cooled
  3. customthen partitioned between EtOAc and 3N HCl
  4. extractionThe organic extract
  5. washwas washed with H2O, saturated NaHCO3 solution, H2O
  6. dry with materialbrine, dried (Na2SO4) and solvent
  7. customremoved in vacuo

Sources & evidence

ORD record
ord-2f256226a2f84a0b987c17a69de4c8d7
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

Loading…