Sodium borohydride → 4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester

HRID 643830노트

반응식

HRID 643830 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[CH:7]=[C:6]1[C:11]([O:13][CH3:14])=[O:12])=[O:4].[BH4-].[Na+]>CO>[CH3:14][O:13][C:11]([CH:6]1[CH2:7][CH:8]([OH:10])[CH:9]=[C:5]1[C:3]([O:2][CH3:1])=[O:4])=[O:12]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 591654631,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylate

생성물 1

HCID 591654434-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester수율 93.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a cold solution (−30° C.) of compound 26 (3.18 g, 16.1 mmol) dissolved in MeOH (23 mL), NaBH4 (0.66 g, 17.5 mmol) was added. After nine minutes the excess of NaBH4 was destroyed by adding brine (80 mL). The mixture was concentrated and extracted with ethyl acetate (4×80 mL). The organic phases were dried, filtrated and concentrated and gave the title compound (3.0 g, 92%) as a yellow oil.

후처리

  1. customAfter nine minutes the excess of NaBH4 was destroyed
  2. additionby adding brine (80 mL)
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate (4×80 mL)
  5. customThe organic phases were dried
  6. filtrationfiltrated
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-766fa764f74d42e29bf13f48c3178ec6
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700552B2

반응 노트

불러오는 중…