Chlorotrimethylsilane → HCID 21848596、化合物

HRID 399311ノート

反応式

HRID 399311 の反応式
[Br:1][C:2]1[C:6]([Br:7])=[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]=1[CH:20]([OH:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24].[H-].[Na+].[H][H].[CH3:36][Si:37](Cl)([CH3:39])[CH3:38]>C1COCC1>[Br:1][C:2]1[C:6]([Br:7])=[C:5]([CH:8]([O:19][Si:37]([CH3:39])([CH3:38])[CH3:36])[C:9]([F:17])([F:18])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[NH:4][C:3]=1[CH:20]([O:31][Si:37]([CH3:39])([CH3:38])[CH3:36])[C:21]([F:29])([F:30])[C:22]([F:27])([F:28])[C:23]([F:26])([F:24])[F:25]

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 21848596HCID 21848596、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'-trimethylsilyloxy-butyl)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-ffc082e835ff4333b4930e31c0dd60d4
出典データセット
uspto-grants-1998_10
特許番号
US05817830

反応ノート

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