HCID 58762434, 화합물 → HCID 58762453, 화합물

HRID 858561노트

반응식

HRID 858561 반응식
[CH:1]1([Mg]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1S[C:15](=[O:24])[CH2:16][CH2:17][C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>CCOCC.C1COCC1>[C:18]1([CH2:17][CH2:16][C:15]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

참가 물질

5

반응물 2

HCID 58762434HCID 58762434, 화합물HCID 178419650HCID 178419650, 화합물

생성물 1

HCID 58762453HCID 58762453, 화합물수율 72%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Cyclopentylmagnesium bromide (1.6 mL, 3.15 mmol, 2M soln in ether) was added to a cooled −78° C. solution of 3-Cyclohex-1-enyl-thiopropionic acid S-pyridin-2-yl ester (0.65 g, 2.63 mmol, from Step 3) dissolved in THF (10 mL). The reaction mixture was stirred for 45 min at −78° C. and then warmed up to rt. The reaction was quenched with 1 N HCl and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound as a clear oil (0.39 g, 72%).

후처리

  1. temperaturewarmed up to rt
  2. customThe reaction was quenched with 1 N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-b538fe3a84614d178d3053b4f9cb81d6
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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