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

HRID 2177809
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HRID 2177809 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2회

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
140 °C

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-b40b7a33196244568886525d95e0d6e1
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067905B2

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