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Boron trifluoride etherate → HCID 22282663, 화합물

HRID 2252743
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HRID 2252743 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH2:11][CH2:10][C:8]3=2)[C:3](=O)[C:2]1=O.[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH2:11][CH2:10][C:8]3=2)[CH:3]=[CH:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 22282700HCID 22282700, 화합물

생성물 1

HCID 22282663HCID 22282663, 화합물수율 42.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

A solution of 2,3,7,8-tetrahydro-1H-furo[2,3-g]indole-2,3-dione (9.05 g, 47.9 mmol) in tetrahydrofuran (100 mL) was stirred at −20° C. under an argon atmosphere. Solid sodium borohydride was added portionwise and the reaction was stirred for 20 min at −20° C. Boron trifluoride etherate (11.9 mL, 96 mmol) was added dropwise over 90 min, then the mixture was warmed to 0° C. and stirred for 1 h. The reaction was quenched with water (100 mL) and the solution was extracted with ethyl acetate (3×150 mL). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo to afford a yellow solid which was purified by column chromatography [SiO2; heptane-ethyl acetate (5:1)] to afford the title compound (3.2 g, 42.8%); analytical data as described above.

후처리

  1. temperaturethe mixture was warmed to 0° C.
  2. stirringstirred for 1 h
  3. customThe reaction was quenched with water (100 mL)
  4. extractionthe solution was extracted with ethyl acetate (3×150 mL)
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow solid which
  8. customwas purified by column chromatography [SiO2; heptane-ethyl acetate (5:1)]

출처 및 근거

ORD 기록
ord-9d649d8b11464fa5a9428ca77ada800d
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07323473B2

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