Imidazole → 2-(5-((Tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid
Reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.O1CCCC1>[Si:17]([O:1][CH2:2][C:3]1[S:7][C:6]([CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 2-[5-(hydroxymethyl)-2-thienyl]acetic acid (500 mg, 2.91 mmol) and imidazole (415 mg, 6.11 mmol) was added tert-butyldimethylsilyl chloride (916 mg, 6.11 mmol) portionwise over 20 minutes. The resultant solution was stirred at room temperature for one hour, tetrahydrofuran (10 mL) was then added and the reaction mixture cooled in an ice-bath. A solution of potassium carbonate (500 mg, 3.62 mmol) in water (10 mL) was added and the reaction mixture stirred for 20 minutes. The reaction solution was diluted with ethyl acetate (30 mL) and washed with brine (2×30 mL). The organic phase was dried over magnesium sulfate, filtered and concentration in vacuo. The residue was purified by silica gel chromatography, eluting with 0-50% ethyl acetate in iso-hexane to give the title compound as a yellow oil (200 mg, 24%) which was used in the next step without further purification.
Workup
- temperaturethe reaction mixture cooled in an ice-bath
- washwashed with brine (2×30 mL)
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentration in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with 0-50% ethyl acetate in iso-hexane
Sources & evidence
- ORD record
- ord-acb38b3438f341b0aed728c4691ac624
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133185B2
Reaction notes
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