Imidazole → 2-(5-((Tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid

HRID 2279947노트

반응식

HRID 2279947 반응식
[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]

참가 물질

8

반응물 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 828856272-[5-(Hydroxymethyl)-2-thienyl]acetic acid

생성물 1

HCID 595637742-(5-((Tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid수율 24%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  1. temperaturethe reaction mixture cooled in an ice-bath
  2. washwashed with brine (2×30 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentration in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-50% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-acb38b3438f341b0aed728c4691ac624
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133185B2

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