3,4-dihydro-2H-pyran → HCID 14537108, compound

HRID 232401Notes

Reaction equation

HRID 232401 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[C:5]([CH2:14][CH:15]=[CH2:16])[CH:4]=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.Cl.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][O:17]2)=[C:5]([CH2:14][CH:15]=[CH2:16])[CH:4]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 145371074-Methoxy-2-(prop-2-en-1-yl)naphthalen-1-olHCID 21584435Pyridinium hydrochloride

Product 1

HCID 14537108HCID 14537108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methoxy-2-(2-propenyl)-1-naphthalenol (0.28 g), dihydropyran (0.60 ml) and pyridinium hydrochloride (32 mg) all in 5 ml of methylene chloride is stirred under a nitrogen atmosphere for 16 hrs at which time TLC analysis indicates the reaction is complete. The solution is poured into 25 ml of saturated aqueous sodium bicarbonate and extracted with ether. The organic phase is washed two times with brine, dried with magnesium sulfate, filtered and concentrated to give 0.42 g of crude product as a yellow oil.

Workup

  1. extractionextracted with ether
  2. washThe organic phase is washed two times with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd6cbe9207b94d4593377c5346ff5e64
Source dataset
uspto-grants-1989_07
Patent number
US04851586

Reaction notes

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