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Tetrahydrofuran → Methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate

HRID 2177809
ノート
印刷プレビュー

反応式

HRID 2177809 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:9]1([S:15]([CH2:18][C:19]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23](OS(C(F)(F)F)(=O)=O)[C:22]([C:37]3[CH:41]=[CH:40][O:39][CH:38]=3)=[CH:21][CH:20]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:42]1COC[CH2:43]1>O>[C:9]1([S:15]([CH2:18][C:19]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([CH2:42][CH3:43])[C:22]([C:37]3[CH:41]=[CH:40][O:39][CH:38]=3)=[CH:21][CH:20]=2)(=[O:16])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2 回

生成物 1

HCID 67108200Methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A mixture of potassium phosphate tribasic (0.244 g), methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate (Intermediate 123, 0.2 g) in THF (2 ml) and water (1 ml) was sealed in a microwave vial and degassed with argon. Palladium (II) chloride dppf complexed with DCM (0.02 g) and triethylborane (0.29 ml) were added and the mixture was heated in the microwave at 140° C. for 15 minutes. After cooling, ethyl acetate and water were added and the organic layer was separated, washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-18% to give methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate (0.092 g) as a white solid.

後処理

  1. customwas sealed in a microwave vial
  2. customdegassed with argon
  3. additionwere added
  4. temperatureAfter cooling
  5. additionethyl acetate and water were added
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-18%

出典と根拠

ORDレコード
ord-b40b7a33196244568886525d95e0d6e1
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067905B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート