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Water → Ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

HRID 926150
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HRID 926150 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:27])[C:8]([CH:20]([OH:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]2[O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S(S([O-])=O)=O.[Na+].[Na+].O>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:27])[C:8]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]2[O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 159087TriacetoxyperiodinaneHCID 87279267Ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)-naphthalen-2-yl)-2-hydroxyacetate

생성물 1

HCID 86691550Ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate (˜8.7 mmol) in CH2Cl2 (40 mL) was added Dess-Martin periodinane (4.07 g, 9.6 mmol). After 1.5 h, a saturated solution of Na2S2O4 (20 mL) and water (20 mL) was added. The mixture was stirred vigorously for 30 min. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give 3 the titled compound. 1H-NMR: 400 MHz, (CDCl3) δ: 8.22 (s, 1H), 7.70 (m, 3H), 4.41 (q, J=7 Hz, 2H), 2.47 (s, 3H), 1.39 (t, J=7 Hz, 3H). 19F-NMR: 377 MHz, (CDCl3) δ: −73.2.

후처리

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-af842949535a4317850dc220c5336849
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284323B2

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