Ethyl bromoacetate → (1RS,3RS)-3-(2-carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

HRID 1279326Notes

Reaction equation

HRID 1279326 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][CH3:24])[CH:19]=2)[CH:14]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[CH2:13]1.Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C)C=O>[C:36]([CH2:35][O:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][CH2:23][CH3:24])[CH:19]=2)[CH:14]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[CH2:13]1)([O:38][CH2:39][CH3:40])=[O:37]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 217130923-(2-Hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

Product 1

HCID 21713104(1RS,3RS)-3-(2-carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (5 mg, 0.21 mmol) in dimethylformamide (0.5 ml) was added (1RS, 3RS)-3-(2-hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (0.058 g, 0.14 mmol) at ice-bath temperature under argon. After stirring for 15 min, ethyl bromoacetate (50 μl, 0.2 mmol) was added and the solution stirred for 1 h at room temperature. The product was partitioned between ethyl acetate and 3M aq HCl. The organic extract was washed with water, sat. aq. NaHCO3 solution and finally brine. After drying (MgSO4 anhydrous) filtration and evaporation followed by chromatography gave (1RS ,3RS)-3-(2-carboethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (0.041 g). The product was dissolved in hot ethanol (10 ml) and 1 M aq. NaOH added (1 ml). The mixture was refluxed for 1 h then cooled, acidified with 6M-aqueous HCl and extracted with ethyl acetate. After evaporation the residue was crystallized from ethyl acetate/hexane to give the title compound (0.035 g, 93%). m.p. 177-178° C.

Workup

  1. stirringthe solution stirred for 1 h at room temperature
  2. customThe product was partitioned between ethyl acetate and 3M aq HCl
  3. extractionThe organic extract
  4. washwas washed with water, sat. aq. NaHCO3 solution and finally brine
  5. customAfter drying
  6. filtration(MgSO4 anhydrous) filtration and evaporation

Sources & evidence

ORD record
ord-3528d93a8540474f8a15a7e7ac12c3f6
Source dataset
uspto-grants-2002_09
Patent number
US06448260B2

Reaction notes

Loading…