Potassium Carbonate → methyl 2-cyclohexylmethyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

HRID 1169340노트

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HRID 1169340 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH:23]1([CH2:29]Br)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[CH:23]1([CH2:29][O:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=3[CH:16]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 22989944methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

생성물 1

HCID 22990052methyl 2-cyclohexylmethyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate수율 78.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (400 mg, 1.83 mmol) dissolved in DMF (8 ml) were added potassium carbonate (507 mg, 3.67 mmol) and cyclohexylmethyl bromide (0.511 ml, 3.66 mmol), and the resulting mixture was stirred at room temperature for 23 hours and at 100° C. for 6 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue and the resulting mixture was extracted with ethyl acetate (×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 15 g, ethyl acetate/hexane=1/19). The objective fractions were concentrated under reduced pressure, hexane was added to the residue and an insoluble material was collected by filtration. The insoluble material was washed with hexane and was then dried under reduced pressure to obtain methyl 2-cyclohexylmethyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (452 mg, 1.44 mmol, 78%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe resulting mixture was extracted with ethyl acetate (×3)
  4. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
  5. concentrationwere then concentrated under reduced pressure
  6. concentrationThe objective fractions were concentrated under reduced pressure, hexane
  7. additionwas added to the residue
  8. filtrationan insoluble material was collected by filtration
  9. washThe insoluble material was washed with hexane
  10. customwas then dried under reduced pressure

출처 및 근거

ORD 기록
ord-17f3f7bf8ca941dcbfc54d52655cf101
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

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