Tetrahydrofuran → 3-(3-Benzyloxy-phenyl)-1-cyclopentyl-propan-1-one

HRID 356530

반응식

HRID 356530 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[Li+].[Cl-].[CH:27]1([Mg]Cl)[CH2:31][CH2:30][CH2:29][CH2:28]1>S(Cl)(Cl)=O.CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 219385043-[3-(Benzyloxy)phenyl]propanoic acidHCID 178478989HCID 178478989, 화합물

생성물 1

HCID 219385753-(3-Benzyloxy-phenyl)-1-cyclopentyl-propan-1-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 24386Thionyl Chloride용매

실험 절차

3-(3-Benzyloxy-phenyl)-propanoic acid (5 g, 19.5 mmol) from Example XXXX was taken up in thionyl chloride (20 mL) and refluxed for 2 hours. The excess thionyl chloride was removed under reduced pressure and carbon tetrachloride added and removed several times under reduced pressure to remove any excess thionyl chloride. The resulting oil was taken up in freshly distilled THF (50 mL), MnCl2 (0.49 g, 3.9 mmol) and LiCl (0.331 g, 7.8 mmol) were added. This was allowed to stir under nitrogen at room temperature until homogenous. The solution was then cooled to 0° C. with an ice bath and 2.0M cyclopentyl magnesium chloride (11.0 mL, 22 mmol) in Et2O was added dropwise to the solution over 0.5 hour. The reaction was allowed to stir for 10 minutes after addition was complete and was then quenched with 1N HCl and brine until acidic. The organics were extracted into EtOAc and then washed with brine and dried with MgSO4. The solvent was removed under reduced pressure and the residue submitted to flash chromatography (3:7 EtOAc:hexane, silica gel) to yield the title compound as a viscous oil. 1H NMR (CDCl3) δ 1.54-1.80 (br m, 8 H), 2.76 (m, 2 H), 2.80 (m, obscured, 1 H), 2.86 (m, 2 H), 5.05 (s, 2 H), 6.81 (br m, 3 H), 7.21 (br m, 1 H), 7.43 (br m, 5 H).

후처리

  1. temperaturerefluxed for 2 hours
  2. customThe excess thionyl chloride was removed under reduced pressure and carbon tetrachloride
  3. additionadded
  4. customremoved several times under reduced pressure
  5. customto remove any excess thionyl chloride
  6. additionwere added
  7. temperatureThe solution was then cooled to 0° C. with an ice bath
  8. stirringto stir for 10 minutes
  9. additionafter addition
  10. customwas then quenched with 1N HCl and brine until acidic
  11. extractionThe organics were extracted into EtOAc
  12. washwashed with brine
  13. dry with materialdried with MgSO4
  14. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-7d75833fb8b64c3ea43df950c4233896
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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