Sodium hydride → HCID 9801173, compound

HRID 2293602Notes

Reaction equation

HRID 2293602 reaction equation
[CH2:1]1[O:32][C:31]2[CH:30]=[CH:29][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)=[C:8]3[C:24]([O:26]CC)=[O:25])=[CH:4][C:3]=2[O:2]1.COC1C=CC(C2C3C(=CC=CC=3)NC=2C(OCC)=O)=CC=1.[H-].[Na+].C(Cl)C1C=CC2OCOC=2C=1>CN(P(N(C)C)(N(C)C)=O)C>[CH2:1]1[O:32][C:31]2[CH:30]=[CH:29][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)=[C:8]3[C:24]([OH:26])=[O:25])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 21476961HCID 21476961, compoundHCID 22676729HCID 22676729, compound

Product 1

HCID 9801173HCID 9801173, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

Ethyl 1-(3,4-methylenedioxybenzyl)-3-(4-methoxyphenyl)indole-2-carboxylate. To a solution of ethyl 3-(4-methoxyphenyl)indole-2-carboxylate (110 mg, 0.37 mmol) in HMPA (2 mL) stirred at ice bath temperature under an argon atmosphere was added NaH (14 mg of 80% oil dispersion, 0.46 mmol, oil removed by pentane wash). After 15 min a solution of piperonyl chloride (128 mg, 0.75 mmol) in HMPA (0.5 mL) was added and the ice bath removed. The reaction mixture was stirred 7 h at room temperature then partitioned between 3N HCl (25 mL) and EtOAc (50 mL). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2SO4). The solvent was removed in vacuo. The residue was purified by chromatography (silica gel, gradient elution from 25% Et2O/hexanes to 45% Et2O/hexanes) to afford the title compound (105 mg, 66%)

Workup

  1. customthe ice bath removed
  2. customthen partitioned between 3N HCl (25 mL) and EtOAc (50 mL)
  3. extractionThe organic extract
  4. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by chromatography (silica gel, gradient elution from 25% Et2O/hexanes to 45% Et2O/hexanes)

Sources & evidence

ORD record
ord-5f81704b5caa445e91b52557355af056
Source dataset
uspto-grants-1997_11
Patent number
US05686481

Reaction notes

Loading…