Triphenylphosphine → 5-Bromo-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester

HRID 533226노트

반응식

HRID 533226 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:11])=[CH:8][C:9]=1[OH:10])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19](O)[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:11])=[CH:8][C:9]=1[O:10][CH:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[Cl:12])[CH3:20])=[O:4]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 260821-(2-Chlorophenyl)ethanolHCID 5462977Diethyl azodicarboxylateHCID 59857018Methyl 5-bromo-3-hydroxythiophene-2-carboxylate

생성물 1

HCID 589704945-Bromo-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester수율 98.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Bromo-3-hydroxy-thiophene-2-carboxylic acid methyl ester (1.67 g, 7/04 mmol, 1.0 Eq.), 1-(2-Chloro-phenyl)-ethanol (1.43 g, 9.16 mmol, 1.3 Eq.) and triphenylphosphine (2.40 g, 9.16 mmol, 1.3 Eq.) were dissolved in anhydrous THF (30 mL) under nitrogen. The resultant solution was cooled to 0° C. and DEAD (1.4 mL, 9.16 mmol, 1.3 Eq.) was added dropwise. The reaction was warmed to ambient temperature and stirred for 4.5 hours. The crude reaction was purified by column chromatography (10% EtOAc/petroleum ether) to give the sub-title compound as a yellow solid (2.60 g, 6.92 mmol, 98%); 1H NMR (400 MHz, CDCl3) δ 1.68 (3H, d), 3.88 (3H, s), 5.71 (1H, q), 6.65 (1H, s), 7.23-7.33 (2H, m), 7.37 (1H, dd), 7.66 (1H, dd).

후처리

  1. customThe crude reaction
  2. customwas purified by column chromatography (10% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-383f6b3f4ba847bfbacfbdf351a5875a
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853244B2

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