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Sodium hydride → Dimethyl [1-acetyl-4,8,12-trimethyltrideca-3,7,11-trienyl]phosphonate

HRID 2379525
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인쇄 미리보기

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HRID 2379525 반응식
[O:1]=[C:2]([CH3:10])[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6].[H-].[Na+].[CH2:13](Br)[CH:14]=[C:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:21])[CH3:16]>C1COCC1>[C:2]([CH:3]([P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6])[CH2:13][CH:14]=[C:15]([CH3:16])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:21])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])(=[O:1])[CH3:10]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 550199Farnesyl bromide

생성물 1

HCID 53770837Dimethyl [1-acetyl-4,8,12-trimethyltrideca-3,7,11-trienyl]phosphonate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

Dimethyl 2-oxopropylphosphonate (560 μL, 4.0 mmol) was added dropwise to a stirred suspension of sodium hydride (50% oil suspension, prewashed with hexane) (210 mg, 4.8 mmol) in anhydrous THF (15 mL) at 20° C. under an Argon atmosphere. The resulting slurry was stirred at 20° C. for 2 hours to allow for complete formation of the sodio derivative and then treated dropwise with farnesyl bromide (1.14 mL, 4.2 mmol). The cloudy yellow mixture was stirred at 20° C. for 2 hours and then quenched with saturated NH4Cl solution. The resulting mixture was washed with water, dried, filtered and evaporated to give the crude product which was purified by flash chromatography on a silica gel column. Elution of the column with hexane:ethyl acetate:methanol (40:10:1, v:v:v) gave the title compound as gum.

후처리

  1. stirringThe cloudy yellow mixture was stirred at 20° C. for 2 hours
  2. customquenched with saturated NH4Cl solution
  3. washThe resulting mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by flash chromatography on a silica gel column
  9. washElution of the column with hexane:ethyl acetate:methanol (40:10:1, v:v:v)

출처 및 근거

ORD 기록
ord-d5939e86e2d841549056d7ee8dc6dc37
출처 데이터셋
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05362906

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