Sodium Hydroxide → 5-[2-Methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylic acid

HRID 2217097

反応式

HRID 2217097 の反応式
[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:3]=1[O:4][C:5]1[O:9][C:8]([C:10]([O:12]C)=[O:11])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][C:3]=1[O:4][C:5]1[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 53397016Methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate2 回

生成物 1

HCID 692212945-[2-Methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylic acid収率 87.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate (Intermediate 4; 217 mg, 0.71 mmol) in methyl alcohol (3 mL) at room temperature was added a solution of sodium hydroxide (126 mg) in water (1 mL) and the reaction stirred for 18 hours. The resulting mixture was concentrated under reduced pressure, the residue taken up in water and extracted into diethyl ether (1×20 mL). The aqueous layer was acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×25 mL). The organic extracts were dried (magnesium sulphate) and concentrated under reduced pressure to give the title compound as a colourless powder (181 mg, 87%). Rf=0.21 (9:1, dichloromethane-methyl alcohol). LCMS Rt=4.33 minutes, m/z=291 (MH+).

後処理

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. extractionextracted into diethyl ether (1×20 mL)
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. dry with materialThe organic extracts were dried (magnesium sulphate)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7207bda33a6d4baaae05f653b539a24a
出典データセット
uspto-grants-2008_08
特許番号
US07407649B2

関連ノート

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