p-Toluenesulfonic acid → HCID 19918040, compound

HRID 1755646Notes

Reaction equation

HRID 1755646 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1>ClCCl>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:6]2[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][O:1][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][O:31]3)[O:4][CH:5]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

Product 1

HCID 19918040HCID 19918040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Hydroxymethyl-5-(4-methoxybenzyloxy)-4-pyrone (2.62 g) was dissolved in dichloromethane (48 ml). To the solution was added, while stirring at room temperature, p-toluenesulfonic acid (100 mg). To the mixture was added dropwise 3,4-dihydro-2H-pyrane (2.28 ml). The mixture was stirred for 3 hours at room temperature. The reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate and an aqueous saline solution, which was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was crystallized from ether, and the crystals were collected by filtration to give 1.85 g of 5-(4-methoxybenzyloxy)-2-(tetrahydropyran-2-yl)oxymethyl-4-pyrone as colorless crystals, m.p.95°-96° C. IR(KBr): 3070, 2940, 1650, 1620, 1510, 1450, 1210, 1020 cm-1. 1H-NMR(DMSO-d6) ε: 1.4-1.8(6H,m), 3.4-3.55(1H,m), 3.65-3.85(4H,m), 4.40(2H,ABq,J=14 Hz), 4.07(1H,br.), 4.86(2H,s), 6.38(1H,s), 6.93(2H,d,J=8 Hz), 7.33(2H,d,J=8 Hz), 8.16(1H,s)

Workup

  1. additionTo the solution was added
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. washThe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate
  4. dry with materialan aqueous saline solution, which was dried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe concentrate was crystallized from ether
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-a43a760557c34f13b8126b4e032816ac
Source dataset
uspto-grants-1995_08
Patent number
US05438053

Reaction notes

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