Toluene → Ethyl 2-hydroxy-2-(3-phenyl-1-benzothiophen-2-yl)acetate
Reaction equation
C([Li])CCC.[C:6]1([C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[O:23].C1(C)C=CC=CC=1>O1CCCC1>[OH:23][CH:22]([C:13]1[S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:12]=1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:21]([O:25][CH2:26][CH3:27])=[O:24]Participants
Procedure
A solution of butyllithium (1.6 M, 3.75 mL, 6 mmol) was added at −20° C. to a solution of 3-phenyl-1-benzothiophene (3a) (1.18 g, 5.61 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere. After 1 hour, a solution of ethyl glyoxylate in toluene (50%, 1.2 mL, 6 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 hours, quenched with water (5 mL) and concentrated in vacuo. The residue was partitioned between dichloromethane (40 mL) and water (15 mL). The organic layer was washed with water (2×15 mL), brine (15 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired alcohol (3b) as a white solid (340 mg, 1.09 mmol, 20%).
Workup
- customquenched with water (5 mL)
- concentrationconcentrated in vacuo
- customThe residue was partitioned between dichloromethane (40 mL) and water (15 mL)
- washThe organic layer was washed with water (2×15 mL), brine (15 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)
Sources & evidence
- ORD record
- ord-428f55417d984109b177d4125c2623a7
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238026B2
Reaction notes
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