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

HRID 47977Notes

Reaction equation

HRID 47977 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c6b018cb360f4f758038cf76d69ba974
Source dataset
uspto-grants-2004_03
Patent number
US06699910B2

Reaction notes

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