Triphenylphosphine → 4-Chloro-3-[2-(4-methoxy-phenyl)-ethoxy]-benzoic acid methyl ester

HRID 967483

反応式

HRID 967483 の反応式
[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.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22]O)=[CH:17][CH:16]=1.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:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH:5]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 697054-Methoxyphenethyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 11819787Methyl 4-chloro-3-hydroxybenzoate

生成物 1

HCID 696523044-Chloro-3-[2-(4-methoxy-phenyl)-ethoxy]-benzoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

g (5.36 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 40 ml of anhydrous tetrahydrofuran. To this solution was added 0.897 g (5.9 mmol) of 2-(4-Methoxy-phenyl)-ethanol, 5.35 g (equivalent to 16.1 mmol PPh3) of triphenylphosphine derivatized polystyrene and 2.80 g (16.1 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 (1/5).

後処理

  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 (1/5)

出典と根拠

ORDレコード
ord-e27f333acdde465189348166545cbaf0
出典データセット
uspto-grants-2005_10
特許番号
US06953857B2

関連ノート

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