Methyl iodide → (2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzyloxy)triisopropylsilane

HRID 2075075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075075
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:5]([CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:4]=1.[H-].[Na+].[CH3:33]I>O1CCCC1>[CH3:33][O:16][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:29])([F:1])[F:30])=[CH:4][C:5]=2[CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:24])[CH3:25])[CH:20]([CH3:22])[CH3:21])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 589686621-(4-(Trifluoromethyl)-2-((triisopropylsilyloxy)methyl)phenyl)cycloheptanol

Produkt 1

HCID 58968723(2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzyloxy)triisopropylsilaneAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-(trifluoromethyl)-2-((triisopropylsilyloxy)methyl)phenyl)cycloheptanol (284 mg; 0.639 mmol) in tetrahydrofuran (3.5 mL) at room temperature was added sodium hydride (40 mg; 1 mmol; 60% dispersion in mineral oil). After stirring at room temperature for 15 minutes methyl iodide (80 uL; 1.28 mmol) was added. Reaction stirred for 16 hours. More sodium hydride (20 mg; 0.5 mmol; 60% dispersion in mineral oil) was added. After 5 minutes methyl iodide (0.1 mL; 1.6 mmol) was added. The reaction was stirred for 16 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water (2×) and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over a 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-15% ethyl acetate in heptanes) to yield 279 mg (95.2%) of the title compound as a colorless oil. MS-GC (El): Calc: 458.6 Found: 439 (M−F). 1H NMR (400 MHz, CDCl3) δ ppm 8.22 (d, J=1.24 Hz, 1H), 7.44 (dd, J=8.30, 1.24 Hz, 1H), 7.34 (d, J=8.30 Hz, 1H), 5.11 (s, 2H), 2.95 (s, 3H), 2.16 (m, 2H), 2.01 (m, 2H), 2.0 (dd, J=14.94, 14.52 Hz, 1H), 1.97 (dd, J=14.94, 14.52 Hz, 1H), 1.83-1.58 (m, 6H), 1.3-1.16 (m, 2H), 1.13 (s, 12H), 1.11 (s, 6H).

Aufarbeitung

  1. additionwas added
  2. customReaction
  3. stirringThe reaction was stirred for 16 hours
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water (2×) and brine
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified over a 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-15% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-ff47d3267d614ab0a866963b4f77b379
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

Notizen zur Reaktion

Wird geladen…