Sodium Hydroxide → 5-phenoxymethyl-1H-pyrazole-3-carboxylic acid

HRID 1724753ノート

反応式

HRID 1724753 の反応式
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:10][N:9]=1)=[O:7])C>CO>[O:14]([CH2:13][C:11]1[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 574528735-phenoxymethyl-1H-pyrazole-3-carboxylic acid ethyl ester

生成物 1

HCID 118454715-phenoxymethyl-1H-pyrazole-3-carboxylic acid収率 88.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Freshly prepared aq. NaOH (10 M in H2O, 10.49 mmol) was added to a stirring, room temperature solution of 41 (0.5164 g, 2.10 mmol) in MeOH (5.2 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (20 min): The reaction was concentrated and then dissolved in 4.2 mL H2O. 10% aq. HCl was added dropwise until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 0.4044 g (88.4%) of 42 as a white solid. Note: An undesired impurity that does not crash out of solution upon HCl addition has a retention time of 9.127 min by 1H (CDCl3, 400 MHz): δ 7.26 (2H, t, J=8.0 Hz), 6.99 (2H, d, J=8.3 Hz), 6.94 (1H, t, J=7.3 Hz), 6.85 (1H, s), 5.10 (2H, s) ppm. 13C (CDCl3, 100 MHz): δ 163.68, 159.73, 146.60, 141.13, 130.51, 122.27, 115.83, 108.88, 63.06 ppm. DEPT (CDCl3, 100MHz): CH2 carbons: 63.06; CH carbons: 130.51, 122.27, 115.83, 108.88 ppm. HPLC: 8.272 min.

後処理

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (20 min)
  4. concentrationThe reaction was concentrated
  5. dissolutiondissolved in 4.2 mL H2O
  6. addition10% aq. HCl was added dropwise until the pH=2
  7. customThe white solid that precipitated from the reaction
  8. filtrationwas filtered off
  9. washwashed with cold H2O
  10. customThe solid was dried under vacuum overnight

出典と根拠

ORDレコード
ord-9194c785cfc84729b026a1c46611d776
出典データセット
uspto-grants-2009_02
特許番号
US07488747B2

反応ノート

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