Sodium Hydroxide → 3-(5-Chlorothiophen-2-yl)propanoic acid

HRID 1432884노트

반응식

HRID 1432884 반응식
[OH-:1].[Na+].[Cl:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:6][CH:5]=1>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][C:11]([OH:1])=[O:12])=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 53788388HCID 53788388, 화합물

생성물 1

HCID 391047953-(5-Chlorothiophen-2-yl)propanoic acid

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 962Water용매

실험 절차

Silver nitrate (117 mg, 0.69 mmol) in 1 mL of H2O is added to 1.36 mL of 1N NaOH at 0° C. and stirred for 5 minutes. To the brown suspension is added 3-(5-chloro-thiophen-2-yl)-propionaldehyde (60 mg, 0.34 mmol) and the resulting mixture is allowed to warm to room temperature over 2 hours. The precipitate is filtered and washed with hot water (2×). The combined aqueous layers are acidified with 6 N HCl and extracted with EtOAc (2×). The combined organic layers are washed with water (2×), then dried over MgSO4, filtered and concentrated in vacuo to give the title compound (50 mg, 0.26 mmol) as a beige solid. The crude material can be used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ6.72 (d, 1H), 6.60 (d, 1H), 3.07 (t, 2H), 2.71 (t, 2H).

후처리

  1. filtrationThe precipitate is filtered
  2. washwashed with hot water (2×)
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers are washed with water (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e820a87cc482495399647f7eb908e7c8
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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