Ethyl Acrylate → Ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate

HRID 2177312ノート

反応式

HRID 2177312 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].CCN(C(C)C)C(C)C>Cl[Pd]Cl.CN(C)C=O>[OH:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:15]=[CH:14]/[C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:3]([C:9]([F:12])([F:11])[F:10])[CH:4]=1

参加物

6

反応物 3

HCID 8821Ethyl AcrylateHCID 81531DiisopropylethylamineHCID 222773074-Bromo-3-(trifluoromethyl)phenol

生成物 1

HCID 90442064Ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-bromo-3-(trifluoromethyl)phenol (5 g, 20.75 mmol, 1.00 equiv), N,N-dimethylformamide (60 mL), ethyl prop-2-enoate (10.5 g, 104.88 mmol, 5.06 equiv), PdCl2 (370 mg, 2.09 mmol, 0.10 equiv), P(tolyl)3 (1.28 g, 4.21 mmol, 0.20 equiv), DIEA (16.25 g). The resulting solution was stirred for overnight at 90° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/8). This resulted in 2.6 g (42%) of ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate as a light yellow solid.

後処理

  1. customInto a 500-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 2.6 g (42%) of ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate as a light yellow solid

出典と根拠

ORDレコード
ord-40226ac7e7a3447c9b9553d7579d2e6e
出典データセット
uspto-grants-2015_06
特許番号
US09067898B1

反応ノート

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