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Water → 7-Methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole-5-carbaldehyde

HRID 2173976
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HRID 2173976 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:29]([OH:32])CO)[C:5]([CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.O>C1COCC1.CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:29]=[O:32])[C:5]([CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2
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참가 물질

5

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HCID 962WaterHCID 86701544(+/-)-1-(7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indol-5-yl)ethane-1,2-diol

생성물 1

HCID 867015437-Methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole-5-carbaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a suspension of (±)-1-(7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indol-5-yl)ethane-1,2-diol (238 mg, 0.52 mmol) in THF (5 mL)/H2O (1 mL) was added NaIO4 (443 mg, 2.1 mmol) at 0° C., and then the mixture was stirred at 0° C. for 1.25 h. The reaction mixture was diluted with EtOAc. The bi-layer was partitioned. The organic phase was washed with half satd. Na2S2O3, H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound with no need of any further purification. 1H NMR (400 MHz, DMSO-d6) δ 10.35 (s, 1H), 8.02 (d, J=4.04 Hz, 1H), 7.68 (d, J=8.59 Hz, 2H), 7.55 (s, 1H), 7.43 (d, J=8.59 Hz, 2H), 7.20 (d, J=4.04 Hz, 1H), 5.27 (d, J=11.62 Hz, 1H), 5.09 (d, J=11.62 Hz, 1H), 4.69-4.76 (m, 1H), 3.68-3.81 (m, 1H), 3.37-3.51 (m, 1H), 2.52 (s, 3H), 2.36 (s, 3H), 1.53-1.70 (m, 2H), 1.32-1.53 (m, 4H).

후처리

  1. customThe bi-layer was partitioned
  2. washThe organic phase was washed with half satd
  3. dry with materialNa2S2O3, H2O and brine, dried over Na2SO4
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-c9d72b1fa5ea40199a50c4950ccb58e7
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056874B2

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