Sodium hydride → HCID 86746851, 화합물

HRID 249126

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HRID 249126 반응식
[H-].[Na+].[C:3]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:6])[CH2:4][CH3:5].[CH2:13](Br)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16]>O1CCCC1>[CH3:16]/[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:14]\[CH2:13][CH:7]([C:3](=[O:6])[CH2:4][CH3:5])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 78656Ethyl 3-oxovalerateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

생성물 1

HCID 86746851HCID 86746851, 화합물수율 77.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a suspension of 3.92 g (97.5 mmol, 3 equiv) of 60% NaH in mineral oil (washed three times with pentane) in 200 mL of tetrahydrofuran at 0° C. under argon was added dropwise a solution of 15.3 mL (107 mmol, 3.3 equiv) of ethyl propionylacetate. After 0.5 hour, a solution of 7.04 g (32.4 mmol) of (E)-geranyl bromide in 20 mL of tetrahydrofuran was added dropwise over 45 minutes. The mixture was stirred one hour at 0° C. and one hour at room temperture, quenched with NH4Cl and diluted with 500 mL of diethyl ether. The organic layer was washed with water and brine, and dried over MgSO4 to obtain 20.157 g of crude product as a yellow oil. Purification by flash chromatography on 800 g of silica gel, eluted with 3:97 ethyl acetate:hexanes provided 7.024 g (77%) of pure product as a clear, colorless oil.

후처리

  1. washin mineral oil (washed three times with pentane) in 200 mL of tetrahydrofuran at 0° C. under argon
  2. customquenched with NH4Cl
  3. additiondiluted with 500 mL of diethyl ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customto obtain 20.157 g of crude product as a yellow oil
  7. customPurification by flash chromatography on 800 g of silica gel
  8. washeluted with 3:97 ethyl acetate

출처 및 근거

ORD 기록
ord-2dc68734c91c44f78cf14d50081558e5
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212164

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