Sodium hydride → (R)-4-[2-nitro-5-(thiophen-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butyric acid

HRID 322918ノート

反応式

HRID 322918 の反応式
[OH:1][C@@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH2:3][CH2:4][C:5]([O-:7])=[O:6].[Na+].[H-].[Na+].F[C:19]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:22]=[CH:21][C:20]=1[N+:32]([O-:34])=[O:33]>C1COCC1>[N+:32]([C:20]1[CH:21]=[CH:22][C:23]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)=[CH:24][C:19]=1[O:1][C@@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])([O-:34])=[O:33]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 220101462-Fluoro-4-(3-thienylmethoxy)nitrobenzeneHCID 86756593Sodium (R)-4-Hydroxy-4-(2-methylphenyl)butanoate

生成物 1

HCID 53638071(R)-4-[2-nitro-5-(thiophen-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butyric acid収率 18.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A stirred suspension of sodium (R)-4-hydroxy-4-(2-methylphenyl)butanoate (190 mg) in THF (15 mL) is treated with 60% sodium hydride (35 mg) and maintained at 25° for 0.5 hours. The mixture is treated with 2-fluoro-4-(thiophen-3-ylmethoxy)nitrobenzene (220 mg) and maintained at 50° C. for 3 hours. The solution is evaporated. The residue is dissolved in ethyl acetate, washed with water, dried and evaporated. The residue is purified by flash chromatography on silica, eluting with dichloromethane followed by ethyl acetate, followed by recrystallisation from ethyl acetate/pentane to give (R)-4-[2-nitro-5-(thiophen-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butyric acid (70 mg), a tan coloured solid, mp. 130-131° C. 1H NMR (CHCl3) 2.2-2.9 (4H,m), 2.4 (3H,s), 4.9 (2H, q), 5.5 (1H, q), 6.2 (1H,s), 6.5 (1H,d), 7.0-7.4 (7H,m), 7.9 (1H,d).

後処理

  1. temperaturemaintained at 25° for 0.5 hours
  2. customThe solution is evaporated
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica
  8. washeluting with dichloromethane
  9. customfollowed by recrystallisation from ethyl acetate/pentane

出典と根拠

ORDレコード
ord-cad6a049ca96463ca497196a04994815
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

反応ノート

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