Benzyl Bromide → 5-(benzyloxy)-2-methoxytetrahydro-2H-pyran

HRID 520396ノート

反応式

HRID 520396 の反応式
[CH3:1][O:2][CH:3]1[O:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.CCOCC>[CH2:13]([O:9][CH:6]1[CH2:7][O:8][CH:3]([O:2][CH3:1])[CH2:4][CH2:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 122006502H-Pyran-3-ol, tetrahydro-6-methoxy-

生成物 1

HCID 857695615-(benzyloxy)-2-methoxytetrahydro-2H-pyran

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

At 0° C. to a solution of 6-methoxytetrahydro-2H-pyran-3-ol (222 mg, 1.680 mmol) in DMF (2 mL) was added 60% NaH (81 mg, 2.02 mmol) and the mixture was allowed to warm to rt and stirred at rt for 30 min. A solution of (bromomethyl)benzene (345 mg, 2.016 mmol) in DMF (1 ml) was added and the mixture was stirred at rt for 18 h. The reaction mixture was diluted with ether and quenched with water. The crude product was purified by silica gel FCC (20% EtOAc in hexanes) to afford 5-(benzyloxy)-2-methoxytetrahydro-2H-pyran. 1H NMR (400 MHz, CDCl3) δ ppm 7.29-7.41 (5H, m), 4.53-4.64 (3H, m), 3.90 (1H, dd, J=12.05, 2.51 Hz), 3.56-3.65 (1H, m), 3.46-3.53 (1H, m), 3.43 (3H, s), 1.97-2.14 (2H, m), 1.69-1.81 (1H, m), 1.48-1.60 (1H, m).

後処理

  1. stirringthe mixture was stirred at rt for 18 h
  2. customquenched with water
  3. customThe crude product was purified by silica gel FCC (20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-fc3594e140664113ae855d9f75a89493
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

反応ノート

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