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

HRID 1169327ノート

反応式

HRID 1169327 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-fc7c4daf70d94818921027d13e88f2d2
出典データセット
uspto-grants-2003_09
特許番号
US06627651B1

反応ノート

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