Sodium hydride → 5-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]1,3-oxazolidin-2-one

HRID 1994497

반응식

HRID 1994497 반응식
[H-].[Na+].[F:3][C:4]([F:22])([F:21])[C:5]1[CH:6]=[C:7]([CH:15]2[O:19][C:18](=[O:20])[NH:17][CH2:16]2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.Br[CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[I:35]>C1COCC1>[F:22][C:4]([F:3])([F:21])[C:5]1[CH:6]=[C:7]([CH:15]2[O:19][C:18](=[O:20])[N:17]([CH2:24][C:25]3[CH:30]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:28]=[CH:27][C:26]=3[I:35])[CH2:16]2)[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 184515342-(Bromomethyl)-1-iodo-4-(trifluoromethyl)benzeneHCID 591350695-[3,5-Bis(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one

생성물 1

HCID 591352395-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A stirred suspension of sodium hydride (60% in oil, 167 mg, 4.18 mmol) in THF (5 mL) was treated at 0° C. with 5-[3,5-bis(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one (500 mg, 1.67 mmol) dissolved in THF (1 mL), under an atmosphere of N2. The reaction was stirred for 20 min and a solution of 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene (610 mg, 1.67 mmol) in THF (1 mL) was added dropwise. The reaction was stirred at room temperature for 18 h. The reaction was quenched with H2O (1 mL) and partitioned between EtOAc (80 mL) and H2O (25 mL). The aqueous phase was re-extracted with EtOAc (2×20 mL) and the combined organic extracts were washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash silica-gel chromatography (0-30% EtOAc in hexanes gradient) to afford 5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]1,3-oxazolidin-2-one. Rf=0.55 (515% EtOAc/hexanes). LCMS 584 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 8.05 (d, J=8.2 Hz, 1H), 7.95 (br s, 1H), 7.85 (br s, 2H), 7.51 (br s, 1H), 7.32 (m, 1H), 5.72 (t, J=8.0 Hz, 1H), 4.74 (d, J=15.5 Hz, 1H), 4.64 (d, J=15.3 Hz), 4.14 (t, J=7.1 Hz, 1H), 3.47 (dd, J=7.1, 1.6 Hz).

후처리

  1. stirringThe reaction was stirred at room temperature for 18 h
  2. customThe reaction was quenched with H2O (1 mL)
  3. custompartitioned between EtOAc (80 mL) and H2O (25 mL)
  4. extractionThe aqueous phase was re-extracted with EtOAc (2×20 mL)
  5. washthe combined organic extracts were washed with brine (30 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThis was purified by flash silica-gel chromatography (0-30% EtOAc in hexanes gradient)

출처 및 근거

ORD 기록
ord-f9315acac83f4ec2b50a6b2d0030392b
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652049B2

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