Hydrochloric Acid → 2-(4-Chlorophenyl)benzoxazole-4-carboxylic acid

HRID 506236ノート

反応式

HRID 506236 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[Li+].Cl>C(OCC)(=O)C.O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68459315Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate

生成物 1

HCID 596258542-(4-Chlorophenyl)benzoxazole-4-carboxylic acid収率 90.3%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 100 mL round bottom flask equipped with a magnetic stirrer was charged with methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate (0.50 g, 1.74 mmol), THF (10 mL), methanol (10 mL), lithium hydroxide (0.08 g, 3.48 mmol) and water (10 mL). The reaction was stirred at room temperature for 18 hours. After this time, the reaction was diluted with ethyl acetate (50 mL) then acidified to pH 4 with 2 N HCl. The aqueous layer was extracted with ethyl acetate (2×25 mL). The organic layers were then combined and washed with brine (1×25 mL), dried with sodium sulfate, filtered and concentrated to dryness in vacuo to yield 2-(4-chlorophenyl)benzoxazole-4-carboxylic acid (0.43 g, 90% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 11.53 (bs, 1H), 8.26 (d, J=8.5 Hz, 2H), 8.18 (d, J=8.0 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.55 (t, J=8.0 Hz, 1H); MS (ESI) m/z 274 [M+H]+

後処理

  1. customA 100 mL round bottom flask equipped with a magnetic stirrer
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×25 mL)
  3. washwashed with brine (1×25 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-abde0d572f164f278a125d46e7c1dae4
出典データセット
uspto-grants-2010_08
特許番号
US07781430B2

反応ノート

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