Sodium Hydroxide → HCID 11058026、化合物

HRID 1609907ノート

反応式

HRID 1609907 の反応式
C([O:3][C:4](=[O:30])[C:5]([CH3:29])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+]>CO>[CH3:29][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:30])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 11025958HCID 11025958、化合物

生成物 1

HCID 11058026HCID 11058026、化合物収率 75.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Methyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid ethyl ester (6.4 g, 15.6 mmol) was dissolved in MeOH (200 mL) and 2N NaOH (150 mL) was added. The resulting cloudy solution became clear after 30 min and the reaction was stirred vigorously overnight. The solution was concentrated under reduced pressure, diluted with H2O (100 mL) and acidified to pH=1 with 5N HCl. The mixture was extracted with EtOAc (2×200 mL), dried (MgSO4), and concentrated under reduced pressure to provide a white solid. The compound was recrystallized from CH3CN (85 mL) to afford the product (4.50 g, 75%) as colorless needles after drying at 50° C. under vacuum for 6 h: Rf=0.14 in 35% EtOAc/hexanes; mp 129-130° C.; 1H NMR (400 MHz, CDCl3) δ 7.98-7.96 (m, 2H), 7.44-7.41 (m, 3H), 6.91-6.79 (m, 4H), 4.16 (t, J=8.8 Hz, 2H), 2.99 (t, J=8.8 Hz, 2H), 2.38 (s, 3H), 1.53 (s, 6H); 13C (100 MHz, CDCl3) δ 177.2, 159.7, 154.7, 148.3, 145.3, 132.4, 130.1, 128.7, 127.2, 126.1, 122.1, 114.9, 79.9, 67.0, 26.1, 25.1, 10.2; IR (CHCl3) 2991, 1775, 1718, 1554, 1506, 1469, 1237, 1145, 1023 cm−1; HRMS (TOF) m/e calcd. for C22H24NO5 (M++1) 382.1654, found 382.1628.

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted with H2O (100 mL)
  3. extractionThe mixture was extracted with EtOAc (2×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto provide a white solid
  7. customThe compound was recrystallized from CH3CN (85 mL)

出典と根拠

ORDレコード
ord-d0752117ac0e42e0ad74d1dead3acace
出典データセット
uspto-grants-2006_01
特許番号
US06982278B2

反応ノート

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