3,4-dihydro-2H-pyran → 2-(3-Bromophenoxy)tetrahydro-2H-pyran

HRID 1734788ノート

反応式

HRID 1734788 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][O:26]2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 115633-BromophenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 50672642-(3-Bromophenoxy)tetrahydro-2H-pyran

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 8.80 g (50.9 mmol) of 3-bromophenol (distilled) and 1.28 g (5.1 mmol) of pyridinium p-toluenesulfonate in 50 ml of dichloromethane was added 6.42 g (7.0 ml, 76.3 mmol) of 3,4-dihydro-2H-pyran. The resulting clear solution was stirred at room temperature for 24 hours, partitioned between 200 ml of water and 400 ml of hexane, and the layers were separated. The organic phase was washed with 100 ml of water, 50 ml of 1N aqueous NaOH solution and 100 ml of brine solution, dried over K2CO3, filtered and concentrated in vacuo to a clear, slightly yellow oil. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) yielded the title compound as a white solid. PMR (CDCl3):d 1.55-2.04 (6H, m), 3.55-3.65 (1H, m), 3.8-3.95 (1H, m), 5.40 (1H, t, J=2.9 Hz), 6.96-7.00 (1H, m), 7.09-7.17 (2H, m), 7.22-7.24 (1H, m).

後処理

  1. custompartitioned between 200 ml of water and 400 ml of hexane
  2. customthe layers were separated
  3. washThe organic phase was washed with 100 ml of water, 50 ml of 1N aqueous NaOH solution and 100 ml of brine solution
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a clear, slightly yellow oil
  7. customPurification by flash chromatography (silica, 5% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-dcf3cbb8821b4546af5f6724c05086ca
出典データセット
uspto-grants-1996_07
特許番号
US05534641

反応ノート

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