Ethyl Acetoacetate → HCID 12354271, compound

HRID 410036Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[C:10](OCC)(=[O:15])[CH2:11][C:12]([CH3:14])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[S:9]2)=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 849893-Methoxybenzenethiol

Product 1

HCID 12354271HCID 12354271, compoundYield 34%

Conditions

Temperature: 110 °C

Procedure

To a mixture of 3-methoxybenzenethiol (24 g, 28.5 mmol) in PPA (200 g) was added ethyl acetoacetate (22.8 g, 28.5 mmol) at room temperature under nitrogen. Then the reaction mixture was heated to 110° C. for 5 h with vigorous stirring and poured into ice-water (100 ml). The resultant mixture was extracted with ethyl acetate (500 ml×3). The combined organic phase was dried with anhydrous sodium sulfate, filtered and concentrated, then purified by silica gel column (PE/EtOAc=10/1) to afford desired product (2 g, 4%) as a yellow solid.

Workup

extractionThe resultant mixture was extracted with ethyl acetate (500 ml×3)
dry with materialThe combined organic phase was dried with anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by silica gel column (PE/EtOAc=10/1)

Sources & evidence

ORD record: ord-2b319e45b87246f4a40394bc23a090a8
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759548B2

Reaction notes

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