Hydrochloric Acid → Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionate

HRID 1598506노트

반응식

HRID 1598506 반응식
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([Cl:21])[C:10]=1[CH:11]=[O:12].COB(OC)OC.Cl>O1CCCC1.[Zn].C(O)(=O)C>[Cl:8][C:9]1[CH:16]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:14]=[C:13]([Cl:21])[C:10]=1[CH:11]([OH:12])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 8470Trimethyl borateHCID 147939142,6-Dichloro-4-(trifluoromethyl)benzaldehyde

생성물 1

HCID 18929422Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionate

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl bromoacetate (13.7 ml) was added to a suspension of 30.0 g of 2,6-dichloro-4-trifluoromethylbenzaldehyde (7), 50 ml of trimethoxyborane and 8.5 g of zinc powder in 50 ml of anhydrous tetrahydrofuran with vigorous stirring at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into a mixture of 100 ml of 10% hydrochloric acid and 10 ml of acetic acid, and the resulting mixture was filtered through Celite. The aqueous filtrate was neutralized with a 5% aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate, drying over anhydrous magnesium sulfate and concentration under reduced pressure, affording 40.7 g of the desired compound in the form of a pale green oil (quantitative crude yield).

후처리

  1. stirringthe mixture was stirred overnight
  2. filtrationthe resulting mixture was filtered through Celite
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialdrying over anhydrous magnesium sulfate and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-7ff1a59db04d47c99c73442c0d25a6a3
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739083

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