Triphenylphosphine → (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester

HRID 987325ノート

反応式

HRID 987325 の反応式
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:18]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH2:54]([O:56][C@@H:57]([CH2:61][C:62]1[CH:67]=[CH:66][C:65](O)=[CH:64][CH:63]=1)[C:58]([OH:60])=[O:59])[CH3:55]>ClCCl>[CH2:17]([O:60][C:58](=[O:59])[C@@H:57]([O:56][CH2:54][CH3:55])[CH2:61][C:62]1[CH:67]=[CH:66][C:65]([O:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([S:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:9][CH:10]=2)=[CH:64][CH:63]=1)[CH3:18]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9837207(2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acidHCID 135676692-(4-Phenylsulfanylphenyl)ethanol

生成物 1

HCID 54503267(S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-[4-(Phenylsulfanyl)phenyl]-1-ethanol (1.22 g; 5.12 mmole), triphenylphosphine (2 g; 7.6 mmole) and 1,1′-(azodicarbonyl)dipiperidine were dissolved in dichloromethane (15 ml). After 10 minutes a solution of (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid (described in Example 40b) in dichloromethane (15 ml) was added and the reaction mixture was stirred over night at room temperature. The solid material was filtered off and the solvent evaporated. Chromatography of the residue on siliga gel using ethyl acetate:petroleum ether (40-60° C.), (1:99, 5:95 and 10:90) gave 1.24 g (yield 47%) of (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester.

後処理

  1. filtrationThe solid material was filtered off
  2. customthe solvent evaporated

出典と根拠

ORDレコード
ord-2622edb8072644899376e8580cfaa27d
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

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