Lithium Hydroxide → 3-(1,3-Thiazol-2-yl)benzoic acid

HRID 2225205노트

반응식

HRID 2225205 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10].[OH-].[Li+]>C1COCC1.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 18945333Methyl 3-thiazol-2-yl-benzoate

생성물 1

HCID 210750873-(1,3-Thiazol-2-yl)benzoic acid수율 72.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Preparation H11, Step 4: A solution of 0.6 g (0.0027 mol) of methyl 3-(thiazol-2-yl)benzoate in 6 ml of THF and 1.2 ml of water was charged with 0.11 g (0.0046 mol) of lithium hydroxide. The reaction mixture was stirred at RT overnight. THF was removed and the aqueous layer was washed with ether and acidified with 1.5 N HCl. The solid product was extracted with ethyl acetate. The organic layer was washed with brine and concentrated to afford 3-(thiazol-2-yl)benzoic acid (0.4 g) as an off white solid obtained. 1H NMR (400 MHz, CDCl3): 7.45 (d, 1H), 7.63 (m, 1H), 8.0 (d, 1H), 8.22 (d, 1H), 8.30 (d, 1H), 8.79 (s, 1H). MS found: (M−H)−=204.

후처리

  1. customPreparation H11, Step 4
  2. customTHF was removed
  3. washthe aqueous layer was washed with ether
  4. extractionThe solid product was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d5814394b779410f801917aba81bf5c6
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378409B2

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