Tetrahydrofuran → HCID 22393666, compound
Reaction equation
[C:1]([C:3]1[CH:7]=[C:6]([CH:8]=[O:9])[S:5][CH:4]=1)#[N:2].O1C[CH2:13][CH2:12][CH2:11]1.C([Mg]Cl)(C)C.C(OCC)(=O)C>CCOCC>[C:1]([C:3]1[CH:7]=[C:6]([CH:8]([OH:9])[CH:12]([CH3:13])[CH3:11])[S:5][CH:4]=1)#[N:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
3-Cyano-5-thiophenecarboaldehyde (2.00 g) was dissolved in anhydrous ether (100 ml) and anhydrous tetrahydrofuran (THF) (20 ml), and an ether solution (10.9 ml) of (2.0 M) isopropylmagnesium chloride was added thereto. After stirring at 0° C. for 2 hours, ethyl acetate was added thereto. The mixture was washed with an aqueous saturated ammonium chloride and further brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a pale yellow oil (1.25 g, 47%).
Workup
- washThe mixture was washed with an aqueous saturated ammonium chloride and further brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)
Sources & evidence
- ORD record
- ord-d2ae3c9b57a54d85ae03c3f092f92b5a
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06906072B1
Reaction notes
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