Chlorotrimethylsilane → Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-

HRID 14454

反応式

HRID 14454 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[O:10][CH2:9][C:8]=2[CH:15]=1)(=[O:3])[CH3:2].C[Si](C)(C)N[Si](C)(C)C.[Na].C[Si](Cl)(C)C.[Br:31]Br>C1COCC1>[Br:31][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[O:10][CH2:9][C:8]=2[CH:15]=1)=[O:3]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 24408BromineHCID 218806101-(2,2-Dimethyl-2,4-dihydro-1,3-benzodioxin-6-yl)ethan-1-oneHCID 45051731Sodium hexamethyidisilazane

生成物 1

HCID 11150315Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the product of step (b) (23.4 g, 0.113 mol) in 600 mL of THF at −78° C. was added 135 mL of 1.0 M sodium hexamethyldisilazane in THF (Sigma-Aldrich). After 1 hour, trimethylsilyl chloride (15.8 mL, 0.124 mol) was added. After another 30 minutes, bromine (5.82 mL, 0.113 mol) was added. After 10 minutes, the reaction was quenched by diluting the reaction mixture with diethyl ether and pouring it onto 500 mL of 5% aqueous Na2SO3 premixed with 500 mL of 5% aqueous NaHCO3. The phases were separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound as an oil that solidified upon storage in the freezer.

後処理

  1. waitAfter another 30 minutes
  2. waitAfter 10 minutes
  3. customthe reaction was quenched
  4. additionby diluting the reaction mixture with diethyl ether
  5. additionpouring it onto 500 mL of 5% aqueous Na2SO3
  6. additionpremixed with 500 mL of 5% aqueous NaHCO3
  7. customThe phases were separated
  8. washthe organic phase was washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ef4ea43a78ff495cb8c3230a83042d2f
出典データセット
uspto-grants-2010_06
特許番号
US07732441B2

関連ノート

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