4-Methoxybenzaldehyde → S-ethyl (E)-3-(4-methoxyphenyl)prop-2-enethioate

HRID 1822516Notes

Reaction equation

HRID 1822516 reaction equation
COc1ccc(C=O)cc1.CCSC(=O)CC(=O)O>C1CCNC1.CN(C)c1ccncc1.C1CCOC1>CCSC(=O)/C=C/c1ccc(OC)cc1

Participants

6

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 127870873-Ethylsulfanyl-3-oxopropanoic acid

Product 1

HCID 101447640S-ethyl (E)-3-(4-methoxyphenyl)prop-2-enethioateYield 74%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineReagentHCID 31268PyrrolidineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °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-6aa603f34669470ab5ee749f8f5ce7fa
Source dataset
Bayesian optimization of 5 decarboxylative olefination reactions

Reaction notes

Loading…