Imidazole → 2-[5-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-2-thienyl]acetic acid

HRID 2279959Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[S:8][C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1>[Si:18]([O:1][CH2:2][CH2:3][C:4]1[S:8][C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[5-(2-hydroxyethyl)-2-thienyl]acetic acid (1.35 g, 7.26 mmol) and imidazole (1.04 g, 15.25) in N,N-dimethylformamide (18 mL) was added tert-butyldimethylsilyl chloride (2.29 g, 15.25 mmol) over 20 minutes. The resultant solution was stirred at room temperature for one hour. Tetrahydrofuran (18 mL) was then added and reaction solution cooled to 0° C. A solution of potassium carbonate (1.04 g, 7.6 mmol) in water (18 mL) was added and the solution stirred for 20 minutes. The reaction solution was then partitioned between ethyl acetate and brine. The organic phases were combined, dried over magnesium sulfate, filtered and concentrated 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 (500 mg, 23%).

Workup

customreaction solution
customThe reaction solution was then partitioned between ethyl acetate and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography
washeluting with 0-50% ethyl acetate in iso-hexane

Sources & evidence

ORD record: ord-25722c27ca444afea69d06427a5365e9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133185B2

Reaction notes

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