Xanthone → 2-Iodoxanthen-9-one

HRID 902986

反応式

HRID 902986 の反応式
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[I:16]N1C(=O)CCC1=O>FC(F)(F)C(O)=O.C(Cl)Cl>[I:16][C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:15])[C:14]=2[CH:1]=1

参加物

4

反応物 2

HCID 7020XanthoneHCID 120273N-Iodosuccinimide

生成物 1

HCID 139791862-Iodoxanthen-9-one収率 54.3%

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

A solution of xanthen-9-one (1.96 g, 10.0 mmol; Aldrich) in trifluoroacetic acid-CH2Cl2 (1:1, 40 mL) was chilled to 0° C. and treated with N-iodosuccinimide (NIS; 2.25 g, 10.0 mmol; Lancaster), added portionwise over 1 h. After an additional 1 h at 0° C., the ice bath was removed and stirring continued for 8 h. Residual oxidant was quenched with aq. NaS2O3 and the mixture was extracted with CH2Cl2. The organic phase was washed with NaHCO3, dried over MgSO4, and the residue purified by flash chromatography (120 g silica gel, 10-100% CH2Cl2-hexanes) to afford the title compound (1.75 g, 5.43 mmol; 54% yield): 1H NMR (300 MHz, CDCl3) δ ppm 8.66 (d, J=2 Hz, 1H), 8.34 (dd, J=8, 2 Hz, 1H), 7.98 (dd, J=9, 2 Hz, 1H), 7.75 (ddd, J=9, 7, 2 Hz, 1H), 7.50 (dd, J=8, 1 Hz, 1H), 7.40 (ddd, J=8, 7, 1 Hz, 1H), 7.28 (d, J=9 Hz, 1H); MS (DCl/NH3) m/z 323 (M+H)+, 340 (M+NH4)+.

後処理

  1. additionadded portionwise over 1 h
  2. customthe ice bath was removed
  3. waitcontinued for 8 h
  4. customResidual oxidant was quenched with aq. NaS2O3
  5. extractionthe mixture was extracted with CH2Cl2
  6. washThe organic phase was washed with NaHCO3
  7. dry with materialdried over MgSO4
  8. customthe residue purified by flash chromatography (120 g silica gel, 10-100% CH2Cl2-hexanes)

出典と根拠

ORDレコード
ord-b0ed738b58704a9c8e0d1ec1ecdc8e14
出典データセット
uspto-grants-2008_04
特許番号
US07365193B2

関連ノート

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