ethyl 2-(4-(cyclopropylthio)phenyl)-2-oxoacetate synthesis
- Product Name:ethyl 2-(4-(cyclopropylthio)phenyl)-2-oxoacetate
- CAS Number:745052-94-2
- Molecular formula:C13H14O3S
- Molecular Weight:250.31
14633-54-6
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745052-94-2
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Yield:745052-94-2 94%
Reaction Conditions:
Stage #1: Ethyl oxalyl chloridewith aluminum (III) chloride in dichloromethane at 0 - 2; for 0.666667 h;
Stage #2: cyclopropylphenylsulfide in dichloromethane at 0 - 20; for 2.75 h;
Steps:
3
Preparation 3: Ethyl (4-cyclopropylsulfanylphenyl)oxoacetate; AICI3 (104.6g, 0.79mol) was suspended in CH2C12 (1.15L) and cooled in an ice/salt bath to 0°C with stirring. Ethyl chlorooxoacetate (84.8g, 0.62mol) was then added over a period of lOmin, during which time the temperature was maintained between 0 and 2°C. The mixture was then stirred for a further 30min at 0°C, before the addition of cyclopropylphenylsulfide (85.0g, 0.57mol) over a period of 45min, during which time the temperature remained between 0 and 8°C. The resulting mixture was allowed to warm to room temperature and stirred for a further 2h. After this time ice/water (275mL) was added, with ice bath cooling maintaining the temperature at 20°C. The organic layer was separated and washed with water (2 x 250mL), saturated NaHC03 solution (2 x 250mL) and again with water (1 x 250mL). The organic fraction was then dried (MgS04) filtered and the solvent removed to provide the title compound (134g, 94% yield). NMR was consistent with the above structure.
References:
WO2006/16178,2006,A1 Location in patent:Page/Page column 10
14633-54-6
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745052-94-2
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$482.00/1g
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745052-94-2
41 suppliers
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