Hydrogen Peroxide → 5-(4-Chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:8][C:9]=1[CH:10]=[CH2:11])=[O:4].C12BC(CCC1)CCC2.[OH:28]O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:8][C:9]=1[CH2:10][CH2:11][OH:28])=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Dissolve 5-(4-chloro-phenyl)-3-vinyl-thiophene-2-carboxylic acid methyl ester (5.35 g, 19.19 mmol) in tetrahydrofuran (220 mL) and cool to 0° C. Slowly add 9-borabicyclo[3.3.1]nonane (112 mL, 0.5 M, 56 mmol), warm the reaction to room temperature with stirring for 16 h. Cool the mixture to 0° C. and slowly add hydrogen peroxide (74 mL, 721 mmol) followed by 5 N sodium hydroxide (74 mL, 370 mmol). Add water (14 mL) and extract with ethyl acetate (3×150 mL). Dry the solution over Na2SO4, filter and evaporate. Purify by chromatography eluting with 50% ethyl acetate/hexane to afford 5.70 g (100%) of the title compound. LC-MS/ES m/z (35Cl) 296.7.0 [M+H]+.
Workup
- customthe reaction to room temperature
- temperatureCool the mixture to 0° C.
- extractionAdd water (14 mL) and extract with ethyl acetate (3×150 mL)
- dry with materialDry the solution over Na2SO4
- filtrationfilter
- customevaporate
- customPurify by chromatography
- washeluting with 50% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-edfeb42d017d49a5b3f4fde9b3d73481
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263772B2
Reaction notes
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