Boron trifluoride etherate → HCID 13866540, 화합물

HRID 1383048노트

반응식

HRID 1383048 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH3:22])=[C:5]([C:18]([O:20][CH3:21])=[O:19])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH2:23]([Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=[CH2:25].B(F)(F)F.CCOCC>C(Cl)(Cl)Cl>[CH3:22][C:4]12[CH2:25][CH:24]([CH2:23][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:7]([C:8]([O:10][CH3:11])=[O:9])([CH:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]1[C:18]([O:20][CH3:21])=[O:19])[C:2]([CH3:1])=[N:3]2

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 129839Dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate

생성물 1

HCID 13866540HCID 13866540, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To 1.0 g (3.3 mmol) dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (1) [B. Loev. et al., J. Med. Chem., 17, 956 (1974)] in 50 ml chloroform cooled in an ice-bath to 0°-5° there was added 7.5 g (66 mmol) commercially obtained allyltrimethylsilane (2) followed by 1.41 g (10 mmol) boron trifluoride etherate added dropwise via syringe. The reaction mixture was then stirred for 4 hours at 0°-10° and quenched by addition of saturated aqueous NaHCO3 solution. After the addition of 50 ml Et2O, the organic phase was separated, washed with brine and dried. Solvent removal left an oil that was purified by column chromatograhy on silica gel eluting with 7% isopropanol/hexane to give pure 3 as of oil, which crystallized after standing, mp. 152°-155°, formula: C23H33NO4Si; m.w., 415.606. mmr (CDCl3) δ 0.78(9H, s), 0.27(1H, dd), 0.47(1H, dd), 0.83(1H, dd), 1.57(3H, s), 2.46(1H, dd), 2.55(3H, s), 2.60(1H, dd), 2.76(1H, m), 3.58(3H, s), 3.74(1H, d), 3.79(3H, s), 7.16(2H, dd), 7.30(3H, m).

후처리

  1. additionadded dropwise via syringe
  2. customquenched by addition of saturated aqueous NaHCO3 solution
  3. additionAfter the addition of 50 ml Et2O
  4. customthe organic phase was separated
  5. washwashed with brine
  6. customdried
  7. customSolvent removal
  8. waitleft an oil that
  9. customwas purified by column chromatograhy on silica gel eluting with 7% isopropanol/hexane
  10. customto give pure 3 as of oil, which
  11. customcrystallized

출처 및 근거

ORD 기록
ord-ee38f4c380bf4b1080d5e0d9b8e388df
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808718

반응 노트

불러오는 중…