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

HRID 39246

反応式

HRID 39246 の反応式
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 1183884-Bromobutanol

生成物 1

HCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyran収率 92.3%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 6344Dichloromethane溶媒

実験手順

3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 1 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 2 as a colorless oil (15.3 g, 92%). 1H NMR (400 MHz, CDCl3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H).

後処理

  1. customAfter removing the solvent
  2. customthe residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-4df15ee16ba343d6858c801aa90a4577
出典データセット
uspto-grants-2013_09
特許番号
US08524691B2

関連ノート

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