Chlorotrimethylsilane → HCID 54338582、化合物

HRID 618888ノート

反応式

HRID 618888 の反応式
Br[C:2]1[C:6](Br)=[C:5]([CH:8]([OH:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[NH:4][C:3]=1C(O)C(F)(F)C(F)(F)C(F)(F)F.[H-].[Na+].[H][H].[CH3:36][Si:37](Cl)([CH3:39])[CH3:38]>C1COCC1>[F:17][C:9]([F:18])([C:10]([F:15])([F:16])[C:11]([F:12])([F:13])[F:14])[CH:8]([C:6]1[CH:2]=[CH:3][NH:4][C:5]=1[CH:8]([O:19][Si:37]([CH3:39])([CH3:38])[CH3:36])[C:9]([F:17])([F:18])[C:10]([F:15])([F:16])[C:11]([F:12])([F:13])[F:14])[O:19][Si:37]([CH3:39])([CH3:38])[CH3:36]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 21848597HCID 21848597、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 54338582HCID 54338582、化合物収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3,4-Dibromo-2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (1 mmol, 0.62 g) was dissolved in 25 ml of dry THF and transferred to a cooled (0° C.) suspension of sodium hydride (2.0 mmol, 0.048 g) in 100 mL of THF. When hydrogen evolution ceased (after 2 hours) trimethylsilyl chloride (2 mmol, 0.218 g) was added by syringe. The mixture was stirred at room temperature overnight before the solvent was removed in vacuo. The remaining residue was partitioned between 10% sodium bicarbonate solution and ether and the organic layer was dried over magnesium sulfate, filtered and evaporated to leave a brown oil. The product was purified by chromatography on silica gel using hexane as eluant. The product was the first material off the column (rf =0.5) The fractions containing this spot were evaporated to leave a colorless oil which solidified upon cooling under vacuum to leave 3,4-dibromo-2,5-(bis(2',2',3',3',4',4',4'-heptafluoro-1'-trimethylsilyloxybutyl)pyrrole as white needles. (380 mg, 50% yield) 1H NMR (360 MHz, CDCl3) 8.84 (broad s, 1 H); 5.30 (dd, 2 H, J1=19.5, J2=1.0); 0.06 (s, 18 H).

後処理

  1. temperaturea cooled
  2. additionwas added by syringe
  3. customwas removed in vacuo
  4. customThe remaining residue was partitioned between 10% sodium bicarbonate solution and ether
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a brown oil
  9. customThe product was purified by chromatography on silica gel
  10. additioncontaining this spot
  11. customwere evaporated
  12. customto leave a colorless oil which
  13. temperatureupon cooling under vacuum

出典と根拠

ORDレコード
ord-03c13b6b0b924a65bac80fb5c24be8b5
出典データセット
uspto-grants-1999_09
特許番号
US05955603

反応ノート

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