Tetrabutylammonium Fluoride → (2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol

HRID 2075076

반응식

HRID 2075076 반응식
[CH3:1][O:2][C:3]1([C:10]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:11]=2[CH2:12][O:13][Si](C(C)C)(C(C)C)C(C)C)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]1([C:10]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][C:11]=2[CH2:12][OH:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 58968723(2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzyloxy)triisopropylsilane

생성물 1

HCID 58968719(2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol수율 92.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyloxy)triisopropylsilane (276 mg; 0.602 mmol) in tetrahydrofuran (3.5 mL) was added tetrabutylammonium fluoride (0.62 mL; 0.62 mmol; 1.0 M solution in tetrahydrofuran). Reaction was stirred at room temperature for 1.5 hours. Solvent was evaporated under reduced pressure. The residue was purified by 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane) to yield 169 mg (92.9%) of the title compound as a colorless gum. MS-GC (El): Calc: 302.3, Found: 302 (M). 1H NMR (400 MHz, CDCl3) δ ppm 7.89 (s, 1H), 7.49 (dd, J=8.30 Hz, 1H), 7.40 (d, J=8.30 Hz, 1H), 5.03 (s, 2H), 3.00 (s, 3H), 2.54 (bs, 1H), 2.23 (m, 2H), 2.04 (m, 2H), 1.88-1.55 (m, 8H).

후처리

  1. customReaction
  2. customSolvent was evaporated under reduced pressure
  3. customThe residue was purified by 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-3d536a653aae4b8098e68dab157c568f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

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