Phenol → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester

HRID 719692노트

반응식

HRID 719692 반응식
C(OC(C1C=C([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:14][CH:13]=2)C=CC=1)=O)C.[CH2:29]([O:31][C:32]([C:34]1[C:35](C2C=CC(CSCCO)=CC=2)=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:33])[CH3:30].C1(O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH2:29]([O:31][C:32]([C:34]1[C:39]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][S:19][CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:16][CH:17]=2)=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33])[CH3:30]

참가 물질

5

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 586105864'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl esterHCID 586105944'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester

생성물 1

HCID 586105774'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester수율 68%

실험 절차

4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was prepared as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (1.65 g, 5.21 mmol, 1 eq.) was treated with phenol (0.69 g, 7.29 mmol, 1.4 eq.), triphenylphosphine (1.91 g, 7.29 mmol, 1.4 eq.), and diisopropyl azidocarboxylate (1.47 g, 1.44 mL, 7.29 mmol, 1.4 eq.). When complete, the reaction was worked up and the product purified by silica gel flash chromatography using 7.5% EtOAc in hexane as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo leaving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (1.40 g, 68% yield) as a yellow oil.

후처리

  1. custom4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was prepared
  2. customthe product purified by silica gel flash chromatography
  3. additionFractions containing the product
  4. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-205cf55e793b4974a0126ffef6531b88
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132456B2

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