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

HRID 2279947ノート

反応式

HRID 2279947 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-acb38b3438f341b0aed728c4691ac624
出典データセット
uspto-grants-2015_09
特許番号
US09133185B2

反応ノート

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