Triacetoxyperiodinane → 5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carbaldehyde

HRID 1028517

반응식

HRID 1028517 반응식
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][OH:21])[CH:9]=1)([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[C:11]([CH:20]=[O:21])=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)[CH:9]=1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 53363647[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol

생성물 1

HCID 578779885'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.725 g of [5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol in 10 mL of CH2Cl2 was added 1.14 g of Dess-Martin periodinane. The mixture was stirred at room temperature for 30 min, then filtered and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 40S column, eluting with 1 CV of 1% EtOAc in hexanes, followed by a linear gradient of EtOAc in hexanes from 1 to 100% over 10 CV to provide the title compound. Mass spectrum (ESI) 323.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 9.81 (s, 1H), 8.28 (s, 1H), 7.88 (dd, J=1.5 Hz, 8 Hz, 1H), 7.54 (d, J=8 Hz, 1H), 7.33 (dd, J=2 Hz, 8 Hz, 1H), 7.16 (d, J=2.5 Hz, 1H), 6.95 (d, J=8.5 Hz, 1H), 3.74 (s, 3H), 2.95 (septet, J=7 Hz, 1H), 1.29 (d, J=7 Hz, 6H).

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on a Biotage Horizon, 40S column
  4. washeluting with 1 CV of 1% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-3f2abf777bbb4b7ea853106cd8094a9f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735435B2

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