3,4-dihydro-2H-pyran → 2-[(4-Bromo-2-ethylbenzyl)oxy]tetrahydro-2H-pyran

HRID 1023411Notes

Reaction equation

HRID 1023411 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][O:29]2)=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 587642724-Bromo-2-ethylbenzenemethanol

Product 1

HCID 867623942-[(4-Bromo-2-ethylbenzyl)oxy]tetrahydro-2H-pyranYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-2-ethylphenyl)methanol (CAS 877131-21-0) (2.8 g, 13 mmol) in methylene chloride (45 mL) were added pyridinium p-toluenesulfonate (327 mg, 1.3 mmol) and 3,4-dihydro-2H-pyran (2.4 mL, 26 mmol) and stirred at RT for 16 h. The reaction mixture was diluted with water, extracted with methylene chloride, dried with magnesium sulfate and concentrated. Purification by MPLC (30% ethyl acetate in hexanes) afforded 2.9 g of Intermediate 1 as a colorless oil.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by MPLC (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ce6ed9f4b3a24f96806020bfe527ff2b
Source dataset
uspto-grants-2014_05
Patent number
US08722712B2

Reaction notes

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