Benzofuran → HCID 21462979, 화합물

HRID 1940550노트

반응식

HRID 1940550 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:25]1([OH:28])[CH:26]=[CH:27][N:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:23]=[CH:24]1

참가 물질

5

반응물 3

HCID 9223BenzofuranHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

생성물 1

HCID 21462979HCID 21462979, 화합물수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of benzofuran (4 g, 33.9 mmol) in tetrahydrofuran (90 ml) at -10° C. was slowly added a solution of n-butyllithium (2.5M in hexanes, 13.6 ml, 34 mmol), keeping the temperature at -10° C. The reaction was stirred and allowed to warm to room temperature over 1 hr, after which a solution of 1-benzyl-4-piperidone (6.3 ml, 34 mmol) in tetrahydrofuran (30 ml) was added dropwise. Stirring was continued for 2 hr at room temperature. The solvent was evaporated and the residue partitioned between saturated aqueous sodium carbonate (75 ml) and ethyl acetate (3×100 ml). The combined organics were dried (MgSO4) and evaporated. The residue was purified by column chromatography, eluting with ethyl acetate, to give 4-(benzofuran-2-yl)-1-benzyl-4-hydroxypyridine (7.5 g, 75%); δH (CDCl3) 1.96-2.00 (2H, m, piperidinyl CH2), 2.21-2.29 (2H, m, piperidinyl CH2), 2.44 (1H, t, J 6.2 Hz, piperidinyl CH), 2.56 (2H, dt, J 11.1, 2.7 Hz, piperidinyl CH2), 2.64-2.68 (3H, m, piperidinyl CH2, OH), 2.73 (1H, t, J 6.2 Hz, piperidinyl CH), 3.55 (2H, s, PhCH2N), 6.58 (1H, s, 3'-H), 7.19-7.34 (7H, m, ArH), 7.44 (1H, d, J 7.3 Hz, ArH), and 7.52 (1H, d, J 6.6 Hz, ArH).

후처리

  1. customat -10° C
  2. stirringStirring
  3. customThe solvent was evaporated
  4. customthe residue partitioned between saturated aqueous sodium carbonate (75 ml) and ethyl acetate (3×100 ml)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-7bb12b27a84c4199bab168337e32b541
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700809

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