Boron trifluoride etherate → HCID 13866540、化合物

HRID 1383048ノート

反応式

HRID 1383048 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 13866540HCID 13866540、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ee38f4c380bf4b1080d5e0d9b8e388df
出典データセット
uspto-grants-1989_02
特許番号
US04808718

反応ノート

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