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

HRID 47977노트

반응식

HRID 47977 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c6b018cb360f4f758038cf76d69ba974
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699910B2

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