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Sodium Thiosulfate → Ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

HRID 926226
ノート
印刷プレビュー

反応式

HRID 926226 の反応式
[CH3:1][C:2]1[C:3]([CH:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.C(O)(C)C>[CH3:1][C:2]1[C:3]([C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:18])([F:19])[F:20])(=[O:16])=[O:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89676528Ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

生成物 1

HCID 89676478Ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

試薬・触媒・溶媒 2

HCID 3776
Isopropanol
溶媒
HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate (˜22.8 g, 56 mmol) in DCM (560 mL) was treated with solid Dess-Martin periodinane (35.7 g, 84.2 mmol) at room temperature. After 60 minutes, isopropyl alcohol (25 mL) was added and allowed to stir for 30 minutes. A mixture of saturated NaHCO3 and saturated Na2S2O3 (100 mL each, diluted to 400 mL with water) was added and the resulting aqueous layer extracted with DCM. The combined organics were washed with water, brine and dried over anhydrous MgSO4 and filtered. Following concentration in vacuo, the residue was purified via Isco silica gel column chromatography (0-35% EtOAc/hex) to afford ethyl 2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate. 1H-NMR: 400 MHz, (CDCl3) δ: 7.98 (d, J=8.4 Hz, 1H); 7.66 (s, 1H); 7.61 (s, 1H); 7.47 (d, J=8.4 Hz, 1H); 4.41 (q, J=7.2 Hz, 2H); 2.55 (s, 3H); 2.49 (s, 3H); 1.40 (t, J=8.4 Hz, 3H).

後処理

  1. additionwas added
  2. extractionthe resulting aqueous layer extracted with DCM
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentration in vacuo
  7. customthe residue was purified via Isco silica gel column chromatography (0-35% EtOAc/hex)

出典と根拠

ORDレコード
ord-6b63afbff1e04b15a039514b77860adf
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284323B2

反応ノート

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