Triphenylphosphine → 4-Chloro-3-[2-(2,4-dichloro-phenyl)-ethoxy]-benzoic Acid Methyl Ester

HRID 967472

반응식

HRID 967472 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([OH:11])[CH:5]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH2:22]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([O:11][CH2:22][CH2:21][C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])[CH:5]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 11819787Methyl 4-chloro-3-hydroxybenzoate

생성물 1

HCID 696522874-Chloro-3-[2-(2,4-dichloro-phenyl)-ethoxy]-benzoic Acid Methyl Ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2.0 g (10.72 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 20 ml of anhydrous tetrahydrofuran. To this solution was added 2.25 g (11.79 mmol) of 2-(2,4-Dichlorophenyl)-ethanol, 10.71 g (equivalent to 32.2 mmol PPh3) of triphenylphosphine derivatized polystyrene and 5.6 g (32.2 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/6).

후처리

  1. filtrationThe polymer was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. washthe solution was washed three times with water
  5. dry with materialThe organic phase was dried with magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/6)

출처 및 근거

ORD 기록
ord-b316ee85efe943cba3f6ed291f32e5cb
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953857B2

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