Benzyl Bromide → Benzyl tetrahydro-2H-pyran-4-carboxylate

HRID 2047471Notes

Reaction equation

HRID 2047471 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 219302Oxane-4-carboxylic acid

Product 1

HCID 23131611Benzyl tetrahydro-2H-pyran-4-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tetrahydro-2H-pyran-4-carboxylic acid (4.8 g) and potassium carbonate (7.6 g) and DMF (73 mL) was added dropwise benzyl bromide (4.6 mL) at 0° C. The reaction mixture was stirred at room temperature for one day, diluted with ice water, and extracted with ethyl acetate. The extract was washed with water, 0.5N hydrochloric acid, water and saturated brine, dried and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (solvent gradient; 0→20% ethyl acetate/hexane) to give benzyl tetrahydro-2H-pyran-4-carboxylate (7.6 g, 94%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, 0.5N hydrochloric acid, water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 0→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b9e07990e8894571ab7ff17da0a066a5
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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