3-Methoxy-3-oxopropanoic acid → HCID 178500105, compound

HRID 2059479Notes

Reaction equation

HRID 2059479 reaction equation
COC(=O)CC(=O)O.COc1ccc2c(c1)c(CC=O)c(C)n2C(=O)c1ccc(Cl)cc1>C1CCNCC1.CN(C)c1ccncc1.CN(C)C=O>COC(=O)/C=C/Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c2ccc(OC)cc12

Participants

6

Reactant 2

HCID 5383663-Methoxy-3-oxopropanoic acidHCID 20158193[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetaldehyde

Product 1

HCID 178500105HCID 178500105, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineReagentHCID 8082PiperidineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Workup

  1. temperatureThe product mixture was cooled to 25 °C.
  2. filtrationFiltered through a pad of celite · Keep Organic
  3. wash"The celite was washed with ethyl acetate (3 x 1 mL)."
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionA 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Sources & evidence

ORD record
ord-e6e6ce7edf2f4016ab4f7d457dacdad4
Source dataset
Transfer learning optimization of 26 decarboxylative olefination reactions

Reaction notes

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