1-(2-Bromophenyl)ethan-1-ol → (1S)-1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)ethanol

HRID 735317

반응식

HRID 735317 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([O-:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[Na+].Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C@@H:29]([OH:31])[CH3:30].N.O>CS(C)=O.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C@@H:29]([OH:31])[CH3:30])(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 69503311-(2-Bromophenyl)ethan-1-olHCID 12896473Azane;hydrateHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

생성물 1

HCID 68899332(1S)-1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)ethanol수율 29.5%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (340 mg, 1.1 mmol), (1S)-1-(2-bromophenyl)ethanol (205 mg, 1.0 mmol) and copper(I) iodide (0.95 g, 4.99 mmol) in dimethyl sulfoxide (10 mL) was degassed and the flask placed in an oil bath at 110° C. The reaction mixture was stirred at this temperature for 2 hours. The cooled reaction mixture was poured into concentrated ammonia/water (1:1; 100 mL) and extracted with diethyl ether (4×50 mL). The extracts were washed with water then brine, combined, dried (MgSO4) and evaporated. The residue was purified by two flash columns, the first eluting with 5-10% diethyl ether/dichloromethane and the second eluting with 40-60% diethyl ether/isohexane, to give the title compound (120 mg, 29%). 1H NMR (500 MHz, CDCl3) δ 8.55 (1H, s), 8.17 (1H, d, J=8.0 Hz), 8.05 (1H, d, J=8.6 Hz), 8.02 (1H, s), 7.97 (1H, d, J=8.7 Hz), 7.84 (1H, dd, J=1.5, 8.5 Hz), 7.76 (2H, d, J=8.4 Hz), 7.69-7.63 (3H, m), 7.49 (1H, t, J=7.2 Hz), 7.19 (2H, t, 8.6 Hz), 5.68-5.62 (1H, m), 2.49 (1H, d, J=3.1 Hz), 1.35 (3H, d, J=6.3 Hz); m/z (ES+) 389 [(M-OH)+].

후처리

  1. customwas degassed
  2. customthe flask placed in an oil bath at 110° C
  3. customThe cooled reaction mixture
  4. extractionextracted with diethyl ether (4×50 mL)
  5. washThe extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by two flash columns
  9. washthe first eluting with 5-10% diethyl ether/dichloromethane
  10. washthe second eluting with 40-60% diethyl ether/isohexane

출처 및 근거

ORD 기록
ord-ce0da753ee3046d0b36ad46408ee600d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592456B2

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