9-Borabicyclo(3.3.1)nonane → cis-Stilbene

HRID 330420

반응식

HRID 330420 반응식
C12BC(CCC1)CCC2.O1CCN(/[C:16](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)CC1>O1CCCC1>[C:18]1(/[CH:17]=[CH:16]\[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

4

반응물 2

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 5358305(e)-1,2-Diphenyl-1-morpholinoethene

생성물 1

HCID 5356785cis-Stilbene수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a mixture of 1.22 g (10.0 mmoles) of solid 9-borabicyclo[3.3.1]nonane (9-BBN) and 2.66 g (10.0 mmoles) of [E]-1-morpholino-1,2-diphenylethene is added 5.0 ml of tetrahydrofuran (THF). The mixture is stirred at 25° C. for 12 hours. The THF is removed under a pressure of about 12 Torr at 25° C. at the end of the 12 hours. The residue is dissolved in 10 ml of methanol and stirred at 25° C. for an additional 12 hours. A by-product, 9-methoxy-9-borabicyclo[3.3.1]nonane morpholine complex crystallizes out of the reaction mixture and is separated by filtration. The methanol is evaporated from the filtrate and the residue is distilled under reduced pressure. The product, 1.17 g of [Z]-1,2-diphenylethene is produced in a yield of 65 percent based on the [E]-1-morpholino-1,2-diphenylethene. The product has a boiling point of 82° C.-84° C. at 0.4 Torr. The stereochemistry of the product is confirmed by 1H and 13C NMR spectroscopy. None of the [E] isomer is detected.

후처리

  1. customThe THF is removed under a pressure of about 12 Torr at 25° C. at the end of the 12 hours
  2. dissolutionThe residue is dissolved in 10 ml of methanol
  3. stirringstirred at 25° C. for an additional 12 hours
  4. customA by-product, 9-methoxy-9-borabicyclo[3.3.1]nonane morpholine complex crystallizes out of the reaction mixture
  5. customis separated by filtration
  6. customThe methanol is evaporated from the filtrate
  7. distillationthe residue is distilled under reduced pressure

출처 및 근거

ORD 기록
ord-fc940f234ca5493e89c4fdbeb3137dd5
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895996

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