p-Toluenesulfonic acid → 2H-Pyran, 2-[(5-bromo-2,2-dimethylpentyl)oxy]tetrahydro-

HRID 47977ノート

反応式

HRID 47977 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:9])([CH3:8])[CH2:6][OH:7].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:9])([CH3:8])[CH2:6][O:7][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 111831775-Bromo-2,2-dimethylpentan-1-ol

生成物 1

HCID 117375402H-Pyran, 2-[(5-bromo-2,2-dimethylpentyl)oxy]tetrahydro-収率 94.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-bromo-2,2-dimethyl-1-pentanol (78 g, 0.35 mol) and p-toluenesulfonic acid (0.42 g) in dichloromethane (0.5 L) was added 3,4-dihydro-2H-pyran (45 mL) slowly at 0° C. The reaction mixture was stirred at rt overnight, or until no more starting material was evidenced by TLC. The mixture was filtered through aluminum oxide and was washed with dichloromethane (300 mL). The filtrate was evaporated under vacuum to produce 5-bromo-1-(tetrahydropyranyloxy)-2,2-dimethylpentane (101 g, 94.7% yield) as a pale-yellow oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 4.48-4.52 (m, 1H), 3.90-3.75 (m, 1H ), 3.50-3.35 (m, 4H), 2.95 (d, J=12 Hz, 1H), 1.90-1.20 (m, 10H), 0.90 (s, 6H). 13C NMR (75 MHz, CDCl3=77.0 ppm/TMS): δ (ppm) 99.2, 76.3, 62.0, 38.0, 34.9, 34.2, 30.7, 28.0, 25.7, 24.8, 24.7, 19.3.

後処理

  1. filtrationThe mixture was filtered through aluminum oxide
  2. washwas washed with dichloromethane (300 mL)
  3. customThe filtrate was evaporated under vacuum

出典と根拠

ORDレコード
ord-c6b018cb360f4f758038cf76d69ba974
出典データセット
uspto-grants-2004_03
特許番号
US06699910B2

反応ノート

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