Lithium Hydroxide → 1-ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid

HRID 2220464ノート

反応式

HRID 2220464 の反応式
C([O:3][C:4]([C:6]1[N:7]([CH2:21][CH3:22])[CH:8]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH:10]=1)=[O:5])C.[Li+].[OH-]>O1CCOCC1>[CH2:21]([N:7]1[CH:8]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH:10]=[C:6]1[C:4]([OH:5])=[O:3])[CH3:22]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 686983271-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid ethyl ester

生成物 1

HCID 686983351-ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid収率 80.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 1-ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid ethyl ester (3.5 g, 11.76 mmol) in dioxane (70 mL) was added LiOH (2M, 35 mL). The reaction mixture was stirred at room temperature for 3 days, and then concentrated in vacuo. The residue was dissolved in H2O (30 ml) and extracted with ether. Under cooling the aqueous was acidified with HCl (3N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and recrystallzation from ether and hexane gave the 1-ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid intermediate as light yellow solid (2.55 g, 79% yield), mp 129° C., 1H NMR (400 MHZ, CDCl3) δ 1.26 (t, 3H), 3.73 (s, 3H), 4.26-4.28 (q, 2H), 6.96-6.97 (m, 2H), 6.99-7.0 (m, 2H), 7.23-7.24 (m, 1H), 7.46 (s, 1H), 12.46 (bs, 1H), MS m/e (M−H)− 268.1.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O (30 ml)
  3. extractionextracted with ether
  4. temperatureUnder cooling the
  5. extractionextracted with EtOAc
  6. dry with materialThe organic extracts were dried over MgSO4
  7. customEvaporation and recrystallzation from ether and hexane

出典と根拠

ORDレコード
ord-7258123e01a7417886e2a48abe16e238
出典データセット
uspto-grants-2008_08
特許番号
US07417047B2

反応ノート

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