Tetrahydrofuran → Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate

HRID 2177774노트

반응식

HRID 2177774 반응식
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:32]1COC[CH2:33]1>O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([CH2:32][CH3:33])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 66685730Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-methoxybenzoate2회

생성물 1

HCID 67107654Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

A mixture of methyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 65, 1.31 g) and potassium phosphate (2.02 g) in THF (9 ml) and water (4.5 ml) was degassed and palladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.6 ml) were added. The mixture was stirred and heated in the microwave at 140° C. for 18 minutes. The mixture was partitioned between ethyl acetate and water and the organic layer was separated, dried (Na2SO4) 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 5-40% to give methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate (0.754 g) as a colourless oil.

후처리

  1. customwas degassed
  2. additionpalladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.6 ml) were added
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customthe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-40%

출처 및 근거

ORD 기록
ord-6a2dd9fbd83a4434918851675b9f302d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

반응 노트

불러오는 중…