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

HRID 1374276ノート

反応式

HRID 1374276 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-99a7580602e346c5b546760458785b0e
出典データセット
uspto-grants-2007_01
特許番号
US07163937B2

反応ノート

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