Allyl bromide → (2S)-1,1-Diphenyl-2-Allyloxy-Pent-4-en

HRID 78920노트

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HRID 78920 반응식
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:8]([OH:12])[CH2:9][CH:10]=[CH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@@H:8]([O:12][CH2:23][CH:22]=[CH2:21])[CH2:9][CH:10]=[CH2:11])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 11390776(2S)-1,1-diphenyl-pent-4-ene-2-ol

생성물 1

HCID 11323419(2S)-1,1-Diphenyl-2-Allyloxy-Pent-4-en수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

(2S)-1,1-diphenyl-pent-4-en-2-ol 25a (0.37 g, 1.57 mmol) was dissolved in dry DMF (2 ml) and was added to a suspension of NaH (60% in mineral oil, 0.13 g, 3.14 mmol) in dry DMF (20 ml) at 0° C. The reaction mixture was allowed to reach room temperature over a period of 1 h. The reaction mixture was cooled again to 0° C. employing an ice-bath, and neat allyl bromide (0.57 g, 4.71 mmol) was added via syringe. The reaction mixture was removed from the ice-bath and stirred overnight at room temperature. The reaction was cooled again to 0° C. and quenched by slowly adding H2O (20 ml). The resulting mixture was extracted with Et2O (3×50 ml), and the combined organic phases were washed in turn with H2O, brine, and then dried over anhydrous Na2SO4. Filtration followed by concentration gave crude product as light orange oil. Purification by chromatography (hexane/ethyl ether=10:1) gave 0.37 g (2S)-1,1-Diphenyl-2-Allyloxy-Pent-4-en (85%, [α]D=([α]D)19.7, c=1, MeOH).

후처리

  1. customThe reaction mixture was removed from the ice-bath
  2. temperatureThe reaction was cooled again to 0° C.
  3. customquenched by slowly adding H2O (20 ml)
  4. extractionThe resulting mixture was extracted with Et2O (3×50 ml)
  5. washthe combined organic phases were washed in turn with H2O, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationFiltration
  8. concentrationfollowed by concentration
  9. customgave crude product as light orange oil
  10. customPurification by chromatography (hexane/ethyl ether=10:1)

출처 및 근거

ORD 기록
ord-3ff5b38dc5c74923a6bddd3c3e51b095
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841464B2

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