Chlorotrimethylsilane → HCID 21848596, 화합물

HRID 399311노트

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HRID 399311 반응식
[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]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 21848597HCID 21848597, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 21848596HCID 21848596, 화합물수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ffc082e835ff4333b4930e31c0dd60d4
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817830

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