Sodium Hydroxide → [4-(3-Phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

HRID 605005노트

반응식

HRID 605005 반응식
C([Si](C)(C)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)(C)(C)C.C([N:27]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][C:39]=1[CH:40]=O)C(=O)C(C)(C)C)=O.[OH-].[Na+]>C(O)C>[C:16]1([C:15]2[C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][OH:6])=[CH:13][CH:12]=3)=[N:27][C:34]3[C:39]([CH:40]=2)=[CH:38][CH:37]=[N:36][CH:35]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 598461331-[4-({[t-Butyl-(dimethyl)silyl]oxy}methyl)phenyl]-2-phenylethanoneHCID 59846154N-formyl-N-(4-formylpyridine-3-yl)-2,2-dimethylpropanamide

생성물 1

HCID 59846130[4-(3-Phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

To a partial suspension of 1-[4-({[t-butyl-(dimethyl)silyl]oxy}methyl)phenyl]-2-phenylethanone (1.03 gm, 3.0 mmol) and N-formyl-N-(4-formylpyridine-3-yl)-2,2-dimethylpropanamide (704 mg, 3.0 mmol) in absolute ethanol (8 mL) was added dropwise 5N NaOH (2.5 mL, 12.5 mmol). This mixture was heated at 70° C. over night. The solvent was evaporated in vacuo and the residue was partitioned between methylene chloride and aqueous sodium carbonate. The organic layer was dried (Na2SO4), the solution filtered, and the solvent evaporated. This residue was chromatographed on a column of silica gel eluting with 40-100% ethyl acetate/hexane and then 0.5-1.5% methanol/ethyl acetate (sat'd with ammonia). The appropriate fractions were combined and the solvents evaporated. The residue was triturated with diethyl ether to give crystalline title compound. 1H-NMR (500 MHz, CDCl3): δ 9.60 (1H, s), 8.65 (1H, d, J=5.5 Hz), 8.17 (1H, s), 7.71 (1H, d, J=5.6 Hz), 7.48 (2H, d, J=6.5 Hz), 7.25-7.36 (7H, m), 4.72 (2H, s). m/e (m+1): 313.2.

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between methylene chloride and aqueous sodium carbonate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationthe solution filtered
  5. customthe solvent evaporated
  6. customThis residue was chromatographed on a column of silica gel eluting with 40-100% ethyl acetate/hexane
  7. customthe solvents evaporated
  8. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-7aaafd8c120f446c9b344a7e502020fe
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

반응 노트

불러오는 중…