Water → 4-[(4-Bromophenyl)methoxy]tetrahydro-2H-pyran

HRID 2304260Notes

Reaction equation

HRID 2304260 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[H-].[Na+].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1.O>CN(C)C=O>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:1][CH:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 226656814-[(4-Bromophenyl)methoxy]tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of 2.90 mL of 4-hydroxy-tetrahydropyran in 30 mL of dry N,N-dimethylformamide was added dropwise to a stirred suspension of 0.84 g of sodium hydride (95%, dispersion in mineral oil) in 30 mL of dry N,N-dimethylformamide at 5° C. The resulting clear solution was allowed to come to room temperature and stirring was continued for 24 hours, followed by dropwise addition of 9.40 g of 4-bromo-benzylbromide in 50 mL of dry N,N-dimethylformamide at 5° C. and stirring at room temperature for 24 hours. The mixture was poured into water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried (sodium sulfate), and concentrated. The residue was purified by silica chromatography (isohexane/ethyl acetate=9/1, 8/2, 7/3, 6/4 v/v) yielding 5.40 g of 4-(4-bromo-benzyloxy)-tetrahydropyran as an oil. EI-MS: 270 (M+).

Workup

  1. customto come to room temperature
  2. stirringstirring at room temperature for 24 hours
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography (isohexane/ethyl acetate=9/1, 8/2, 7/3, 6/4 v/v)

Sources & evidence

ORD record
ord-5e23bfd6940649ceb3af3492054a4096
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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