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Sodium hydride → HCID 21476978, compound

HRID 2293606
Notes
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Reaction equation

HRID 2293606 reaction equation
[C:1]([CH2:6][O:7][C:8]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:9]=1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)=[C:12]1[C:33]([O:35]CC)=[O:34])([O:3]CC)=[O:2].C(COC1C=C(OC)C=CC=1CN1C2C(=CC(O)=CC=2)C(C2C=CC3OCOC=3C=2)=C1C(OCC)=O)(OCC)=O.[H-].[Na+].ICCC>CN(C=O)C>[C:1]([CH2:6][O:7][C:8]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:9]=1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)=[C:12]1[C:33]([OH:35])=[O:34])([OH:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 21476971HCID 21476971, compoundHCID 21476972Ethyl 1-(2-carboethoxymethoxy-4-methoxybenzyl)-5-hydroxy-3-(3,4-methlenedioxyphenyl)indole-2-carboxylate

Product 1

HCID 21476978HCID 21476978, compoundYield 47%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 1-(2-Carboethoxymethoxy-4-methoxybenzyl)-3-(3,4-methlenedioxyphenyl)-5-(prop-1-yloxy)indole-2-carboxylate. To a solution of ethyl 1-(2-carboethoxymethoxy-4-methoxybenzyl)-5-hydroxy-3-(3,4-methylenedioxyphenyl)indole-2-carboxylate (175 mg, 0.30 mmol) in DMF stirred at ice bath temperature under an argon atmosphere was added a slurry of NaH (11 mg of 80% oil dispersion, 0.36 mmol, oil removed by pentane wash) in DMF (1 mL). After 15 min at ice bath temperature, 1-iodopropane (0.255 g, 1.5 mmol) was added and the ice bath was removed. The reaction mixture was stirred an additional 30 min at room temperature then partitioned between 3N HCl (25 mL) and EtOAc (75 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 and the resulting solid crystallized from EtOH to afford the title compound (83 mg 47%); m.p. 89°-91° C.

Workup

  1. customthe ice bath was removed
  2. customthen partitioned between 3N HCl (25 mL) and EtOAc (75 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 resulting solid crystallized from EtOH

Sources & evidence

ORD record
ord-2d3b872481914e04ba2687623c54f4d0
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05686481

Reaction notes

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