Hydrochloric Acid → 1-Benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylic acid

HRID 1952524노트

반응식

HRID 1952524 반응식
[CH2:1]([N:8]1[C:12]([C:13]#[C:14][C:15]([OH:28])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:11]([CH:29]=[O:30])[CH:10]=[C:9]1[C:31]([O:33]C)=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.O>[CH2:1]([N:8]1[C:12]([C:13]#[C:14][C:15]([OH:28])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:11]([CH:29]=[O:30])[CH:10]=[C:9]1[C:31]([OH:33])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86664849Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 866648501-Benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
60 °C

실험 절차

To a solution of 6 (0.49 g, 1.1 mmol) in MeOH (20 mL) and water (6 mL) was added KOH (0.18 g, 3.3 mmol) and stirred at 60° C. for 2 hours. The solvent was removed in vacuo. The residue obtained was acidified with 2N HCl to pH 2-3 and extracted with EtOAc (3×15 mL). The combined organic layer was dried over MgSO4, filtered and then concentrated in vacuo to give 7 as a light brown solid. The crude product was subjected to the next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 7.50-7.52 (m, 4H), 7.45 (s, 1H), 7.21-7.26 (m, 7H), 7.02-7.03 (m, 2H), and 5.64 (s, 2H).

후처리

  1. customThe solvent was removed in vacuo
  2. customThe residue obtained
  3. extractionextracted with EtOAc (3×15 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-55da00aca94b44baa3c105f3beac0faa
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404728B2

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