Cyanic acid → Dibenzyl ether

HRID 1981230Notes

Reaction equation

HRID 1981230 reaction equation
[H-].[Na+].[C:3]([OH:5])#N.[CH2:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[CH2:6]([O:5][CH2:3][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 540Cyanic acidHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 1.1 g of sodium hydride (21 mmole, 50% oil dispersion in 25 ml of dry DMF at 0° C. was added a solution of 3.34 g of title F cyanoalcohol (20 mmole) in 10 ml of DMF over a period of 10 minutes. After stirring for an additional 15 minutes, 3.6 g of benzyl bromide was added dropwise. The reaction mixture was stirred for 30 minutes at 0° C. and 3 hours at 25° C. then quenched with a saturated ammonium chloride solution, and diluted with ether. The organic layer was washed with brine. The combined aqueous layer was re-extracted with ether. The combined organic layer was dried over anhydrous MgSO4 and concentrated to leave an oil. The crude oil was chromatographed on a silica gel column, eluting with 10-20% ethyl acetate in hexanes to give 4.43 g of the title G benzyl ether.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes at 0° C. and 3 hours at 25° C.
  2. customthen quenched with a saturated ammonium chloride solution
  3. additiondiluted with ether
  4. washThe organic layer was washed with brine
  5. extractionThe combined aqueous layer was re-extracted with ether
  6. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customto leave an oil
  9. customThe crude oil was chromatographed on a silica gel column
  10. washeluting with 10-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-02968713200b460da060c4950aa5e3f0
Source dataset
uspto-grants-1985_04
Patent number
US04513103

Reaction notes

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