Benzyl Bromide → Methyl 7-benzyloxy-8-n-propylchroman-2-carboxylate

HRID 1285254Notes

Reaction equation

HRID 1285254 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:15]([O:17][CH3:18])=[O:16])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[CH2:25]([O:1][C:2]1[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:15]([O:17][CH3:18])=[O:16])[O:9]2)=[CH:4][CH:3]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13537867Methyl 3,4-dihydro-7-hydroxy-8-propyl-2H-1-benzopyran-2-carboxylate

Product 1

HCID 14882998Methyl 7-benzyloxy-8-n-propylchroman-2-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 250 ml single neck round bottom flask was charged with 5.25 g (21 mmole) of methyl 7-hydroxy-8-n-propylchroman-2-carboxylate, 150 ml of dimethylformamide, 3.59 g (26 mmole) of anhydrous potassium carbonate, and 4.30 g (25 mmole) of benzyl bromide. The flask was stoppered and stirred (magnetic stirrer) at room temperature for 4 hours. The insoluble solids were separated by filtration and the dimethylformamide removed by rotary evaporation. The residue was dissolved in 200 ml ethyl acetate, clarified by filtration, and concentrated to an oily residue by rotary evaporation. The resultant crude material was purified by high pressure liquid chromatography (5% ethyl acetate-hexane), to obtain 5.48 g (77%) of the title compound as a clear oil. Calc: C, 74.09; H, 7.11; Found; C, 74.11; H, 7.06.

Workup

  1. customThe insoluble solids were separated by filtration
  2. customthe dimethylformamide removed by rotary evaporation
  3. dissolutionThe residue was dissolved in 200 ml ethyl acetate
  4. filtrationclarified by filtration
  5. concentrationconcentrated to an oily residue by rotary evaporation
  6. customThe resultant crude material was purified by high pressure liquid chromatography (5% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-90a9aece90f54b1599a89f9c3c7d3017
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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