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

HRID 2379525
ノート
印刷プレビュー

反応式

HRID 2379525 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d5939e86e2d841549056d7ee8dc6dc37
出典データセット
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05362906

反応ノート

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