Methanol → 1,1-Diphenyl-10-undecen-1-ol

HRID 275464노트

반응식

HRID 275464 반응식
[C:1]([O:13]CC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>C1COCC1>[C:16]1([C:1]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 12729Ethyl 10-undecenoateHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 200883261,1-Diphenyl-10-undecen-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 10.6 g of ethyl undecylenate in 100 mL of THF at 0° C. was added, over 1 hr, 40 mL of 3M phenyl magnesium bromide. The mixture was warmed to room temperature and stirred for 75 hrs. Methanol, 10 mL, was added to quench the excess Grinard reagent and the solvent was distilled in vacuo. The residue was shaken with diethyl ether and dilute hydrochloric acid. The ether layer was washed with water and saturated sodium hydrogen carbonate, dried, and concentrated in vacuo to give 18.3 g of crude product, which was then chromatographed on silica gel with chloroform as the eluent, to give 13.7 g of 1,1-diphenyl-10-undecen-1-ol which is characterized by:

후처리

  1. customto quench the excess Grinard reagent
  2. distillationthe solvent was distilled in vacuo
  3. stirringThe residue was shaken with diethyl ether and dilute hydrochloric acid
  4. washThe ether layer was washed with water and saturated sodium hydrogen carbonate
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give 18.3 g of crude product, which
  8. customwas then chromatographed on silica gel with chloroform as the eluent

출처 및 근거

ORD 기록
ord-6cb8f2f55a024083988d5d0bfd71aa31
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393795

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