Hydrochloric Acid → 2-[3-[4-(Trifluoromethyl)phenethyloxy]-4-methoxybenzyl]butyric acid

HRID 1826093ノート

反応式

HRID 1826093 の反応式
[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:11]=1)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=2)[CH:11]=1)[C:4]([OH:6])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11144343Ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]propanoate

生成物 1

HCID 111013452-[3-[4-(Trifluoromethyl)phenethyloxy]-4-methoxybenzyl]butyric acid収率 88.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]propanoate (793 mg, 1.87 mmol), methanol (20 mL) and 1 mol/L aqueous solution of sodium hydroxide (10 mL) was stirred for 4 hours at 60° C. After cooling, ice water (50 mL) was added and the mixture was made acidic with 1 mol/L hydrochloric acid, which was then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1 v/v) to afford 654 mg (88%) of the title compound as colorless crystals. Further, these were recrystallized from diethyl ether-n-hexane, thus obtaining 391 mg of the purified title compound as colorless needles.

後処理

  1. temperatureAfter cooling
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1 v/v)

出典と根拠

ORDレコード
ord-7b611c8b19654b2f8b1ba79db308bb75
出典データセット
uspto-grants-2006_05
特許番号
US07049342B2

反応ノート

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