Benzyl 4-[di(ethoxycarbonyl)methoxy]indole-1-carboxylate → Diethyl 2-(indol-4-yloxy)malonate

HRID 16571Notes

Reaction equation

HRID 16571 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2C(OCC1C=CC=CC=1)=O)=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[NH:12]1[C:13]2[C:9](=[C:8]([O:7][CH:6]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11]1

Participants

5

Reactant 2

HCID 11539127Benzyl 4-[di(ethoxycarbonyl)methoxy]indole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 11608989Diethyl 2-(indol-4-yloxy)malonateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 12 (8.51 g, 20 mmol) in ethanol (250 mL) was mixed with 10% palladium on carbon (1.5 g) and hydrogenated at atmospheric pressure for 1 h until hydrogen uptake ceased. The catalyst was filtered off through a Celite bed and washed with ethanol, and the filtrate was evaporated to give a brown oil. Filtration through flash silica with ethyl acetate-hexanes (3:2) as eluent, followed by trituration with diethyl ether-hexanes at −20° C. gave 8 as white crystals (4.78 g, 82%), mp 52-53° C. (from diethyl ether-hexanes), identical to the material described above.

Workup

  1. filtrationThe catalyst was filtered off through a Celite bed
  2. washwashed with ethanol
  3. customthe filtrate was evaporated
  4. customto give a brown oil
  5. filtrationFiltration through flash silica with ethyl acetate-hexanes (3:2) as eluent
  6. customfollowed by trituration with diethyl ether-hexanes at −20° C.

Sources & evidence

ORD record
ord-7f7079dbc6c542e0b73345abbb196625
Source dataset
uspto-grants-2010_06
Patent number
US07737169B2

Reaction notes

Loading…