Hydrochloric Acid → 4-[2-(Ethoxycarbonyl)vinyl]phenylacetic Acid

HRID 1937052ノート

反応式

HRID 1937052 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.Cl>CN(C)C=O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)(=O)C>[CH2:17]([O:16][C:12]([CH:13]=[CH:14][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1)=[O:15])[CH3:18]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 74654Benzeneacetic acid, 4-bromo-HCID 81531Diisopropylethylamine

生成物 1

HCID 696934804-[2-(Ethoxycarbonyl)vinyl]phenylacetic Acid

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 4-bromophenylacetic acid (43.0 g, 200 mmol) in dimethyl formamide (400 mL) in a round bottom flask under nitrogen atmosphere at room temperature was added ethyl acrylate (43.3 mL, 400 mmol), palladium diacetate (0.90 g, 4 mmol), triphenylphosphine (2.10 g, 8 mmol), and diisopropylethylamine (87.2 mL, 500 mmol). The reaction mixture was heated to 100° C. for 43 hours, cooled to room temperature, and hydrochloric acid (1N, 1 L) was added. To the reaction mixture was added ethyl acetate (500 mL), the aqueous layer was extracted with ethyl acetate (2×500 mL), and the combined organic layers washed with hydrochloric acid (1N, 500 mL), water (500 mL) and saturated sodium chloride solution (250 mL), then dried over sodium sulfate, filtered and evaporated in vacuo to provide the title compound as a mixture of cis and trans isomers (46.9 g, 100%).

後処理

  1. temperaturecooled to room temperature
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×500 mL)
  3. washthe combined organic layers washed with hydrochloric acid (1N, 500 mL), water (500 mL) and saturated sodium chloride solution (250 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-943b533c564d4a0f86ba98c6ea776576
出典データセット
uspto-grants-2002_05
特許番号
US06392053B2

反応ノート

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