Hydrochloric Acid → HCID 22227947、化合物

HRID 1526947ノート

反応式

HRID 1526947 の反応式
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]C)=[O:16].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[CH:4][C:3]=1[C:15]([OH:17])=[O:16]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89740836methyl 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylate

生成物 1

HCID 22227947HCID 22227947、化合物収率 36.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

A mixture of methyl 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylate (177 mg, 0.72 mmol), lithium hydroxide monohydrate (111 mg, 2.62 mmol), tetrahydrofuran (5 mL), methanol (1 mL) and water (1 mL) was stirred at 20° C. for 4 hours. The mixture was acidified to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (15 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuum and separated by HPLC (condition: column AD-H (20 mm*250 mm*5 μm), hexane:ethanol (0.2% DEA)=50:50, flow rate: 13 mL/min) to give 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylic acid (60 mg, 36%). LRMS (M+H+) m/z: calcd. 230.11; found 230.

後処理

  1. extractionextracted with ethyl acetate (15 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuum
  5. customseparated by HPLC (condition: column AD-H (20 mm*250 mm*5 μm), hexane:ethanol (0.2% DEA)=50:50, flow rate: 13 mL/min)

出典と根拠

ORDレコード
ord-66c8306ad5fe4b81849db35b2d939e17
出典データセット
uspto-grants-2015_07
特許番号
US09085583B2

反応ノート

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