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

HRID 1429190노트

반응식

HRID 1429190 반응식
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][C:10](=[O:12])[CH:9]=[C:8]1[C:13]([O:15][CH3:16])=[O:14])=[O:6]>CO>[CH3:16][O:15][C:13]([CH:8]1[CH2:9][CH:10]([OH:12])[CH:11]=[C:7]1[C:5]([O:4][CH3:3])=[O:6])=[O:14]

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

NaBH4 (0.66 g, 17.5 mmol) dissolved in MeOH (23 mL) was added to a cold solution (−30° C.) of the ketone 23a (3.18 g, 16.1 mmol). 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 which 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 which

출처 및 근거

ORD 기록
ord-12facf2eb21845baa7e9cba33c1b1533
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937080B2

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