Ethyl formate → HCID 58470771, compound
Reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]2[CH2:26][CH2:25][CH:24]3[CH:19]([CH:20]=[CH:21][CH2:22][CH2:23]3)[S:18]2)=[CH:12][CH:11]=1.[CH:27](OCC)=[O:28].[Cl-].[NH4+]>C1COCC1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[S:18][CH:19]3[CH:24]([CH2:25][C:26]=2[CH:27]=[O:28])[CH2:23][CH2:22][CH:21]=[CH:20]3)=[CH:14][CH:15]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
3.0 ml of lithium diisopropyl amide (1.5 mol/l of THF/cyclohexane solution) was dropped into 20 ml of anhydrous THF solution including 0.84 g of (4-chlorophenyl)-(3,4,4a,5,6,8a-hexahydro-thiochromene-2-ylidene)-amine under nitrogen atmosphere at −78° C. After stirring at −78° C. for 30 minutes, 2 ml of THF solution including 0.34 g of ethyl formate was dropped into the resulting solution. The solution was stirred at room temperature for one additional hour, and added with saturated ammonium chloride aqueous solution, extracted with ethyl acetate. The organic layer was washed with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain crude 2-(4-chloro-phenylamino)-4a,5,6,8a-tetrahydro-4H-thiochromene-3-carbaldehyde.
Workup
- customat −78° C
- additionwas dropped into the resulting solution
- stirringThe solution was stirred at room temperature for one additional hour
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried with anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d977ba603dff47edbe998c6a988b4386
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222430B2
Reaction notes
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