Benzyl Bromide → Ethyl acetate hexane

HRID 2184342Notes

Reaction equation

HRID 2184342 reaction equation
[H-].[Na+].O[CH2:4][C@H:5]1[O:9][C:8](=[O:10])[CH2:7]C1.C(Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[C:8]([O:9][CH2:5][CH3:4])(=[O:10])[CH3:7].[CH3:16][CH2:17][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2733813(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone

Product 1

HCID 21226206Ethyl acetate hexaneYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

40 mL of DMF were added to 1.27 g (31.67 mmol, 60% dispersion in mineral oil) NaH and 5.26 g (31.67 mmol) KI at 0° C. under N2. A solution of 3.50 g (30.16 mmol) of (S)-(+)-dihydro-5-hydroxymethyl-2(3H)furanone (Aldrich) in 15 mL of DMF was then added drop wise. Slurry was allowed to warm to room temperature and stir for 2.5 hours, 5.4 mL (45.24 mmol) benzyl bromide were then added drop wise and mixture was heated to 50° C. and allowed to stir for 16 hours. Reaction was partitioned between 250 mL saturated NH4Cl(aq) and 250 mL ethyl acetate/hexane (60%). Organic layer was washed with water (3×200 mL), 200 mL brine, dried over Magnesium Sulfate and concentrated under reduced pressure. Crude residue was purified via chromatography, eluting with 35% ethyl acetate/hexane yielding 3.37 g (16.34 mmol, 54% yield) (S)—O-Benzyl-dihydro-5-hydroxymethyl-2(3H)furanone as a yellow oil. Step 2

Workup

  1. customat 0° C.
  2. temperaturemixture was heated to 50° C.
  3. stirringto stir for 16 hours
  4. customReaction
  5. customwas partitioned between 250 mL saturated NH4Cl(aq) and 250 mL ethyl acetate/hexane (60%)
  6. washOrganic layer was washed with water (3×200 mL), 200 mL brine
  7. dry with materialdried over Magnesium Sulfate
  8. concentrationconcentrated under reduced pressure
  9. customCrude residue was purified via chromatography

Sources & evidence

ORD record
ord-7e3715bcf484428096f2fba53ce66a10
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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