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Chlorotrimethylsilane → HCID 21848610, 화합물

HRID 399310
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HRID 399310 반응식
[F:1][C:2]([F:17])([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)[OH:4].[H-].[Na+].[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>C1COCC1>[F:17][C:2]([F:1])([C:10]([F:15])([F:16])[C:11]([F:12])([F:13])[F:14])[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)[O:4][Si:21]([CH3:23])([CH3:22])[CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 104006151H-Pyrrol-2-yl(perfluoropropyl)methanol

생성물 1

HCID 21848610HCID 21848610, 화합물수율 92.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2-(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (2.6514 g, 10 mmol) dissolved in 25 ml of dry THF was transferred by canula to a suspension of sodium hydride (0.2640 g, 11 mmol) in 50 ml of THF. The mixture was stirred for 2 hours at room temperature. Trimethylsilyl chloride (1.195 g, 11 mmol) was added dropwise and the solution was stirred overnight. The resulting suspension was evaporated almost to dryness and 50 ml of water was added. The mixture was extracted 3×50 mL with pentane and the organic layers were combined and dried over magnesium sulfate. Upon standing the MgSO4 withdrew a brown impurity from solution leaving a colorless organic layer. The solvent was evaporated leaving a light brown oil (3.128 g). 1H NMR showed that the crude material was 96% product by weight. The overall yield was therefore calculated to be 89%. 1H NMR (CDCl3, 360 MHz) 8.43 (broad s, 1 H); 6.83 (m, 1 H); 6.22 (m, 1 H) 6.17 (q, 1 H, J=2.8 Hz) 5.16 (dd, 1 H, J1=18.5 Hz, J2=5.8 Hz); 0.03 (s, 9 H)

후처리

  1. stirringthe solution was stirred overnight
  2. customThe resulting suspension was evaporated almost to dryness and 50 ml of water
  3. additionwas added
  4. extractionThe mixture was extracted 3×50 mL with pentane
  5. dry with materialdried over magnesium sulfate
  6. customwithdrew a brown impurity from solution
  7. customleaving a colorless organic layer
  8. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-fc4b433861644eb3b9b49b46d15d4fb8
출처 데이터셋
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05817830

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