Methanol → 4-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid

HRID 1991155ノート

反応式

HRID 1991155 の反応式
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:32])C.C1COCC1.CO.[OH-].[Na+]>CCOC(C)=O.Cl>[F:30][C:28]([F:29])([F:31])[C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([S:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:33])=[O:3])=[C:8]([CH3:32])[CH:9]=3)=[CH:15][CH:16]=2)=[CH:23][CH:24]=1

参加物

7

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 207681104-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

生成物 1

HCID 225550394-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid収率 86.8%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A 1 L round-bottomed flask was charged with compound 7.4 (40.9 g, 85.8 mmol), THF (100 mL) and MeOH (100 mL). Next, 2 N NaOH (86 mL, 172 mmol) was added dropwise, and the reaction was stirred at room temperature for 1 h. The solution was neutralized with 2 N HCl (86 mL) and the organic solvent was evaporated to give an aqueous solution and an insoluble oil. The residue was diluted with AcOEt (300 mL) and 1N HCl (300 mL), and partitioned. The organic phase was successively washed with water (400 mL) and brine (400 mL), dried over MgSO4, and concentrated to give white crystals. Recrystallization from 520 mL of AcOEt/hexane (3/10) gave compound 7 (33.4 g) as white crystals. MS APSI m/e: 447 (M−H). 1H NMR (400 MHz) (DMSO-d6) δ 13.0 (1H, brs); 7.64 (2H, d, J=8.8 Hz); 7.38 (2H, d, J=8.3 Hz); 7.30-7.20 (2H, m); 7.16 (4H, d, J=8.3 Hz); 6.89 (1H, d, J=8.5 Hz); 5.14 (2H, s); 4.74 (2H, s); 2.19 (3H, s).

後処理

  1. customthe organic solvent was evaporated
  2. customto give an aqueous solution
  3. custompartitioned
  4. washThe organic phase was successively washed with water (400 mL) and brine (400 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give white crystals
  8. customRecrystallization from 520 mL of AcOEt/hexane (3/10)

出典と根拠

ORDレコード
ord-a0c8f58372464157bc3c57e684b1b2a8
出典データセット
uspto-grants-2010_01
特許番号
US07645779B2

反応ノート

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