Benzyl Bromide → HCID 86731481, compound

HRID 1773028Notes

Reaction equation

HRID 1773028 reaction equation
[CH3:1][O:2][C:3]1([C:10]([OH:12])=[O:11])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1([C:10]([O:12][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:11])[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86731482HCID 86731482, compound

Product 1

HCID 86731481HCID 86731481, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a flask containing 1-methoxy-4-oxocyclohexanecarboxylic acid (0.253 g, 1.469 mmol) was added potassium carbonate (0.406 g, 2.94 mmol). The mixture was diluted with DMF (5 mL) and benzyl bromide (0.192 mL, 1.616 mmol) was added. The mixture was heated to 60° C. for 15.5 h, then cooled to rt, diluted with water (20 mL), and extracted with ethyl acetate (20 mL). The organic layer was washed with water three times, then with sat. aq. NaCl, and was finally 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 0-50% EtOAc in hexanes gradient and a 12 g silica gel column to give the title product (0.294 g, 1.12 mmol, 76% yield). 1H NMR (500 MHz, CHLOROFORM-d) δ=7.41-7.31 (m, 5H), 5.23 (s, 2H), 3.35 (s, 3H), 2.62-2.53 (m, 2H), 2.37-2.28 (m, 4H), 2.19-2.10 (m, 2H).

Workup

  1. additionwas added
  2. temperaturecooled to rt
  3. extractionextracted with ethyl acetate (20 mL)
  4. washThe organic layer was washed with water three times
  5. dry with materialwith sat. aq. NaCl, and was finally dried over magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-49bae75efc0a40a181c17056c21ecbf5
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

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