Water → 3-(3-Oxocyclobutyl)propanoic acid

HRID 511603

반응식

HRID 511603 반응식
[O:1]=[C:2]1[CH2:5][CH:4]([CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])[CH2:3]1.O.[OH-].[Na+]>CO>[O:1]=[C:2]1[CH2:5][CH:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:3]1

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67775333Ethyl 3-(3-oxocyclobutyl)propanoate

생성물 1

HCID 677753573-(3-Oxocyclobutyl)propanoic acid수율 94%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of ethyl 3-(3-oxocyclobutyl)propanoate (200 mg, 1.18 mmol) in methanol (4 mL) was treated with water (0.75 mL) and a 2N solution of sodium hydroxide (0.75 mL, 1.41 mmol) and the solution was heated at 55° C. till the starting material was consumed by TLC (25% EA/hept). After 1 h the starting material was found to be consumed. The reaction mixture was cooled to room temperature and concentrated to remove the MeOH. The aqueous phase was diluted with 2 mL H2O and made acidic to pH˜2 with 1N HCl. The solution was saturated with NaCl and extracted with three 10 mL portions of ethyl acetate. The organic phase was dried over Na2SO4, filtered and concentrated to yield the title compound (157 mg, 94%) as a light orange viscous oil that was used as is in the next step: GC purity 63.2% (ret. time, 4.27 min).

후처리

  1. customwas consumed by TLC (25% EA/hept)
  2. customto be consumed
  3. concentrationconcentrated
  4. customto remove the MeOH
  5. additionThe aqueous phase was diluted with 2 mL H2O
  6. extractionextracted with three 10 mL portions of ethyl acetate
  7. dry with materialThe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d6717f638c6e49a0a652ce62ac9a13fc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096634B2

연결된 노트

불러오는 중…