Tetrahydrofuran → HCID 67272822, 화합물

HRID 250984

반응식

HRID 250984 반응식
CCO[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[CH3:12])=[O:5].[CH3:13][CH2:14][Mg+].[Br-].[CH2:17]1COC[CH2:18]1>>[CH3:12][C:7]1[C:6]([C:4]([OH:5])([CH2:13][CH3:14])[CH2:17][CH3:18])=[CH:11][CH:10]=[CH:9][N:8]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 74401Ethyl 2-methylnicotinateHCID 178461630HCID 178461630, 화합물

생성물 1

HCID 67272822HCID 67272822, 화합물수율 40%

실험 절차

To a stirred solution of ethyl 2-methyl nicotinate (1.04 g, 6.30 mmol) in dry THF (30 mL) was slowly added EtMgBr (3.0 M in Et2O, 5.2 mL, 16 mmol). The mixture was warmed to reflux and stirred for 60 h under N2. The suspension was cooled, poured into ice (50 mL) and stirred for 3 h. The layers were separated, and the aqueous layer was extracted with Et2O (5×100 mL). The combined organic layers were dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2), affording 3-(2-methyl-pyridin-3-yl)-pentan-3-ol as a yellow solid (0.447 g, 40%). 1H NMR (CDCl3) δ 0.77 (t, 6H, J=7.5 Hz), 1.80-2.12 (m, 4H), 2.70 (s, 3H), 7.12 (dd, 1H, J=4.8, 7.8 Hz), 7.87 (dd, 1H, J=7.8, 1.5 Hz), 8.39 (dd, 1H, J=4.8, 1.5 Hz).

후처리

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. temperatureThe suspension was cooled
  4. stirringstirred for 3 h
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with Et2O (5×100 mL)
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. filtrationAfter filtration the solvent
  9. customwas removed by evaporation under vacuum
  10. customthe residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2)

출처 및 근거

ORD 기록
ord-ca76cef1d78a4aafb01efc9473836ad7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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