Triphenylphosphine → 3-[2-(2,4-Dichlorophenyl)-ethoxy]-4-methoxy-benzoic Acid Methyl Ester

HRID 1831773ノート

反応式

HRID 1831773 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([OH:31])[CH:24]=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][CH2:54]O>C1COCC1>[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:54][CH2:53][C:47]2[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]=2[Cl:45])[CH:24]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 693063413-[2-(2,4-Dichlorophenyl)-ethoxy]-4-methoxy-benzoic Acid Methyl Ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

20 g of triphenylphosphine and 10 g of 3-Hydroxy-4-methoxy-benzoic acid methyl ester were dissolved in 200 ml of anhydrous THF. The solution was cooled to 0° C. to 10° C. and a solution of 11.4 ml DEAD in 30 ml anhydrous THF was added dropwise over 20 min. The reaction was warmed to RT and stirred for 45 min. A solution of 11.3 ml 2-(2,4-Dichlorophenyl)-ethanol in 10 ml anhydrous THF was added with cooling. The reaction was stirred at RT for 16 h, and then the solvents were removed under reduced pressure. The residue was treated with n-heptane:ethyl acetate/1:1. The filtrate was dried under reduced pressure. The product was purified by silica gel chromatography, eluting with n-heptane:ethyl acetate/4:1, then n-heptane:ethyl acetate/3:1.

後処理

  1. temperatureThe solution was cooled to 0° C. to 10° C.
  2. temperaturewith cooling
  3. stirringThe reaction was stirred at RT for 16 h
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was treated with n-heptane
  6. customThe filtrate was dried under reduced pressure
  7. customThe product was purified by silica gel chromatography
  8. washeluting with n-heptane

出典と根拠

ORDレコード
ord-fa31fc515036472d8917d2ca484fff6e
出典データセット
uspto-grants-2006_06
特許番号
US07067665B2

反応ノート

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