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

HRID 2220464노트

반응식

HRID 2220464 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7258123e01a7417886e2a48abe16e238
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417047B2

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