3,4-dihydro-2H-pyran → HCID 53778239, compound

HRID 1166727Notes

Reaction equation

HRID 1166727 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][O:14][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 13291510HCID 13291510, compound

Product 1

HCID 53778239HCID 53778239, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-bromo-4-(2-hydroxyethyl)naphthalene (1.71 g, 6.8 mmol) in dichloromethane (20 mL) was added 3,4-dihydro-2H-pyrane (1 mL, 0.92 g, 11.0 mmol) and p-toluene sulfonic acid (80 mg). The mixture was stirred at room temperature for 90 min, diluted with dichloromethane (20 mL), washed with satd. NaHCO3 sol. (20 mL), dried (MgSO4), and concentrated. Flash chromatography using hexane/ethyl acetate 9:1 as eluent provided 1.69 g (75%) of a colorless oil.

Workup

  1. washwashed with satd
  2. dry with materialNaHCO3 sol. (20 mL), dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-911c688311dd4a0b8d87a546bf14d7d7
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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