Benzyl cyclopent-3-enecarboxylate → Benzyl 3-hydroxycyclopentanecarboxylate

HRID 1160611노트

반응식

HRID 1160611 반응식
[CH:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.B1([O-])O[O:17]1.O.O.O.O.[Na+]>C1COCC1>[OH:17][CH:3]1[CH2:4][CH2:5][CH:1]([C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:2]1

참가 물질

4

반응물 2

HCID 22084261Benzyl cyclopent-3-enecarboxylateHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

생성물 1

HCID 14530758Benzyl 3-hydroxycyclopentanecarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

The benzyl cyclopent-3-ene-1-carboxylate (2.0 g, 9.89 mmol) was dissolved in 20 mL of THF and cooled to 0° C. under nitrogen. Borane-THF complex (0.95 mL, 9.89 mmol) was added via syringe and the mixture was stirred for 30 minutes at 0° C. Sodium perborate tetrahydrate solution (100 mL of 0.33 M aqueous solution) was added, and after 30 minutes the reaction mixture was extracted with ethyl acetate. The combined extracts were washed with water and brine and then dried over sodium sulfate. Filtration and concentration provided the crude product which was purified by chromatography on silica gel eluting with 10 to 30% EtOAc in hexanes to provide benzyl 3-hydroxycyclopentanecarboxylate.

후처리

  1. additionBorane-THF complex (0.95 mL, 9.89 mmol) was added via syringe
  2. extractionafter 30 minutes the reaction mixture was extracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration
  6. customprovided the crude product which
  7. customwas purified by chromatography on silica gel eluting with 10 to 30% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-8d292544f4b64ee49c924bd93fb0e600
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816380B2

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