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

HRID 2217097

반응식

HRID 2217097 반응식
[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

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 53397016Methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate2회

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7207bda33a6d4baaae05f653b539a24a
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407649B2

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