Water → 2-(6-bromo-3-(methoxymethoxy)-2-propylbenzyloxy)tetrahydro-2H-pyrane

HRID 552447Notes

Reaction equation

HRID 552447 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][CH3:11])[C:3]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.[H-].[Na+].[CH3:22][O:23][CH2:24]Cl.O>CN(C)C=O>[Br:1][C:2]1[C:3]([CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[C:4]([CH2:9][CH2:10][CH3:11])[C:5]([O:8][CH2:22][O:23][CH3:24])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 579007894-bromo-2-propyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenol

Product 1

HCID 579008212-(6-bromo-3-(methoxymethoxy)-2-propylbenzyloxy)tetrahydro-2H-pyraneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-propyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenol (972 mg, 2.95 mmol) in N,N-dimethylformamide (5 mL), sodium hydride (55% in oil, 257 mg, 5.90 mmol) and chloromethyl methyl ether (475 mg, 5.90 mmol) were added at 0° C. The mixture was stirred at room temperature for 2 hours. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (910 mg, 83%) was obtained as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-572e798be4db4dffbd1fbe998b40b971
Source dataset
uspto-grants-2011_05
Patent number
US07951822B2

Reaction notes

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