Benzyl Bromide → HCID 12827154, compound

HRID 1485836Notes

Reaction equation

HRID 1485836 reaction equation
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH:3]=[CH:2]1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH:2]=[CH:3]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5508252-Cyclohexene-1,4-diol

Product 1

HCID 12827154HCID 12827154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 34 (79 mg, 0.69 mmol) in DMF (1 mL) was added sodium hydride (14 mg, 0.62 mmol) at 0° C. Benzyl bromide (73 μL, 0.62 mmol) was added to the mixture dropwise, under an argon atmosphere. The reaction was stirred for 16 h at room temperature. Upon completion, distilled water (3 mL) was added to the mixture and the organic layer extracted into ethyl acetate. The organic layers were combined, dried and concentrated to give a crude mixture that was purified by column chromatography (Silica gel, 10%-20% EtOAc in hexane) to give 35 as an oil.

Workup

  1. distillationUpon completion, distilled water (3 mL)
  2. additionwas added to the mixture
  3. extractionthe organic layer extracted into ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude mixture that
  7. customwas purified by column chromatography (Silica gel, 10%-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-ec927e1369724cf0bc30af60a8959100
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

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