Sodium Hydroxide → 3-Cyclopropyl-benzo[b]thiophene-2-carboxylic acid

HRID 57163노트

반응식

HRID 57163 반응식
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[CH:15]1[CH2:17][CH2:16]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH:15]1([C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[C:4]([OH:5])=[O:3])[CH2:16][CH2:17]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 59651664HCID 59651664, 화합물

생성물 1

HCID 579205163-Cyclopropyl-benzo[b]thiophene-2-carboxylic acid수율 79.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of compound 674-B (2.68 g, 10.9 mmol) in ethanol (30 mL) was treated with 3N aqueous sodium hydroxide (5.4 mL, 16.2 mmol) and refluxed for 2 h. The solution was cooled, and the solvent was evaporated in vacuo. The residue was dissolved in water and washed with dichloromethane. The aqueous phase was acidified with concentrated hydrochloric acid, and the product was extracted into ethyl acetate, washed with brine, dried over Na2SO4, filtered and the solvent was evaporated in vacuo, to afford 1.9 g of compound 674-C as a colorless solid. 1H-NMR (DMSO-d6): δ 0.58-1.37 (m, 4H), 2.44-2.47 (m, 1H), 7.13-7.61 (m, 2H), 7.98 (dd, 2H), 13.33 (br s, 1H).

후처리

  1. temperaturerefluxed for 2 h
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. washwashed with dichloromethane
  6. extractionthe product was extracted into ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-7456505ad86047e18f51e8dc985b56d3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434711B2

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