Benzyl Bromide → HCID 86731480, compound

HRID 1773027Notes

Reaction equation

HRID 1773027 reaction equation
[CH2:1]([O:3][C:4]1([C:11]([OH:13])=[O:12])[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[CH2:1]([O:3][C:4]1([C:11]([O:13][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:12])[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1)[CH3:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86731478HCID 86731478, compound

Product 1

HCID 86731480HCID 86731480, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-ethoxy-4-oxocyclohexanecarboxylic acid (0.777 g, 4.17 mmol) in DMF (15 mL) was added potassium carbonate (1.153 g, 8.35 mmol) followed by benzyl bromide (0.546 mL, 4.59 mmol). The mixture was heated at 60° C. for 18 h, then cooled to rt. The mixture was diluted with water (30 mL) and extracted with ethyl acetate (2×30 mL). The organic layers were washed with water (3×30 mL), then with brine and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography using a 0-25% ethyl acetate in hexanes gradient and a 24 g silica gel column to give benzyl 1-ethoxy-4-oxocyclohexanecarboxylate (0.9 g, 3.26 mmol, 78% yield) as a light-yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.40-7.32 (m, 5H), 5.21 (s, 2H), 3.48 (q, J=6.9 Hz, 2H), 2.65-2.54 (m, 2H), 2.39-2.27 (m, 4H), 2.20-2.09 (m, 2H), 1.24 (t, J=7.0 Hz, 3H).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe organic layers were washed with water (3×30 mL)
  4. dry with materialwith brine and dried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0a606ea925d143f989e53dd921094a5d
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

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