Potassium Carbonate → methyl 2-(4-fluorobenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

HRID 1169327노트

반응식

HRID 1169327 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+].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][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)=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 22989944methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

생성물 1

HCID 22989984methyl 2-(4-fluorobenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate수율 99.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (327 mg, 1.50 mmol) dissolved in DMF (6 ml) were added potassium carbonate (415 mg, 3.00 mmol) and 4-fluorobenzyl bromide (0.206 ml, 1.65 mmol), and the resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate (40 ml) was added to the residue and the resulting mixture was washed with water (5 ml×3) and an aqueous saturated solution of sodium chloride (5 ml). The organic layer was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 15 g, ethyl acetate/hexane=1/25). The objective fractions were concentrated under reduced pressure to obtain methyl 2-(4-fluorobenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (485 mg, 1.49 mmol, 99%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (40 ml)
  2. additionwas added to the residue
  3. washthe resulting mixture was washed with water (5 ml×3)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. concentrationThe objective fractions were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fc7c4daf70d94818921027d13e88f2d2
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

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