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Reaction
4-Methoxybenzaldehyde → S-ethyl (E)-3-(4-methoxyphenyl)prop-2-enethioate
HRID
1822504
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Reaction equation
COc1ccc(C=O)cc1.CCSC(=O)CC(=O)O>C1CCNC1.CN(C)c1ccncc1.Cc1ccccc1>CCSC(=O)/C=C/c1ccc(OC)cc1
Participants
Conditions
Workup
Sources & evidence
Reaction notes
Participants
6
Reactant
2
HCID
31244
4-Methoxybenzaldehyde
HCID
12787087
3-Ethylsulfanyl-3-oxopropanoic acid
Product
1
HCID
101447640
S-ethyl (E)-3-(4-methoxyphenyl)prop-2-enethioate
Yield 80%
Reagents, catalysts & solvents
3
HCID
14284
4-(Dimethylamino)pyridine
Reagent
HCID
31268
Pyrrolidine
Catalyst
HCID
1140
Toluene
Solvent
Conditions
Temperature
50 °C
Workup
temperature
The product mixture was cooled to 25 °C.
filtration
Filtered through a pad of celite · Keep Organic
wash
"The celite was washed with ethyl acetate (3 x 1 mL)."
concentration
The filtrate was concentrated under reduced pressure
addition
A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.
Sources & evidence
ORD record
ord-ea7532b6e99d4563a58ec8c332f2b300
Source dataset
Bayesian optimization of 5 decarboxylative olefination reactions
DOI
10.26434/chemrxiv.15001213
Reaction notes
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