3,4-dihydro-2H-pyran → HCID 14537113, compound

HRID 232405Notes

Reaction equation

HRID 232405 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[OH:18])=[O:2].[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.Cl.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[O:18][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:19]1)=[O:2]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 14537112HCID 14537112, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 14537113HCID 14537113, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 76 mg of 2-(3-formylpropyl)-4-methoxy-1-hydroxynaphthalene in 2 ml methylene chloride is treated with 0.5 ml of dihydropyran and then with a few mg of pyridinium hydrochloride. The resulting solution is stirred at room temperature for 24 hrs at which time TLC analysis indicates no remaining starting material. The solution is poured into 20 ml of saturated aqueous sodium bicarbonate and extracted two times with ether. The combined organic extracts are washed with water (pH adjusted to 7 with 10% aqueous sodium bisulfate), dried with magnesium sulfate, filtered and concentrated to give 173 mg of crude product.

Workup

  1. extractionextracted two times with ether
  2. washThe combined organic extracts are washed with water (
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-83eb4452d5a4480696acee596afb4e69
Source dataset
uspto-grants-1989_07
Patent number
US04851586

Reaction notes

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