Hydrochloric Acid → 3,5-Bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)benzoic acid ethyl ester

HRID 324052ノート

反応式

HRID 324052 の反応式
C(N[C:14](=[O:45])[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[C:18]([O:31][CH2:32][CH2:33][OH:34])=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)[CH:16]=1)CCCCCCCCCCC.C[N+]1([O-])CC[O:50][CH2:49][CH2:48]1.OS([O-])=O.[Na+].Cl>CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:49]([O:50][C:14](=[O:45])[C:15]1[CH:16]=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:42])[F:43])[CH:36]=2)[C:18]([O:31][CH2:32][CH2:33][OH:34])=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=2)[CH:20]=1)[CH3:48]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 82029Methyl morpholine oxide2 回HCID 22237575N-dodecyl-3,5-bis(m-trifluoromethylphenyl)4-(2-hydroxyethoxy)benzamideHCID 23665763Sodium Bisulfite

生成物 1

HCID 540981933,5-Bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)benzoic acid ethyl ester収率 44.6%

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒2 回HCID 6342Acetonitrile溶媒

実験手順

To a solution of N-dodecyl-3,5-bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)benzamide (0.254 g, 0.40 mmol) in CH3CN was added NMO (0.145 g, 0.89 mmol) and TPAP (0.014 g, 0.04 mmol). The reaction was stirred at room temperature overnight. Additional NMO (0.045 g, 0.38 mmol) and TPAP (0.013 g, 0.04 mmol) were required as indicated by TLC. After stirring 48 h, 10% NaHSO3 solution was added and the resulting biphasic mixture was stirred vigorously for 30 min. Conc. HCl (2 mL) was added and stirring was continued for 10 min. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:Hexane+1% Formic acid) followed by preparatory plate chromatography (30% EtOAc:Hexane+1% Formic acid) to afford the title compound (0.089 g, 34%) as a white solid. mp 154.3-158.2° C.; 1H NMR (DMSO-d6) δ8.55 (t, 1H); 7.98-7.88 (m, 6H); 7.78-7.67 (m, 4H); 3.57 (s, 2H); 3.25 (m, 2H); 1.50 (m, 2H); 1.23 (m, 18H); 0.82 (t, 3H); IR (KBr) 3275, 2900, 1725, 1600, 1575, 1460, 1325, 1190, 1125, 1075, 775, 725, 700, 625 cm−1; mass spectrum [(−)ESI], m/z 650 (M−H)−; Anal. Calcd. for C35H39F6NO4: C, 64.51; H, 6.03; N, 2.15, Found: C, 62.50; H, 5.99; N, 2.01.

後処理

  1. stirringAfter stirring 48 h
  2. stirringthe resulting biphasic mixture was stirred vigorously for 30 min
  3. stirringstirring
  4. waitwas continued for 10 min
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (30% EtOAc:Hexane+1% Formic acid)

出典と根拠

ORDレコード
ord-e1470e89e21b49c3ba45bec09bad7bf1
出典データセット
uspto-grants-2001_04
特許番号
US06214877B1

反応ノート

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