Sodium hydride → HCID 19384432, compound

HRID 2399737Notes

Reaction equation

HRID 2399737 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[CH:19]=[CH:18][C:15](CBr)=[CH:14][CH:13]=1>C1COCC1>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[CH:13]=[C:14]([CH:15]=[CH:18][CH:19]=1)[CH2:4][O:3][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:6]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Product 1

HCID 19384432HCID 19384432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-cyclohexan-1-ol (0.63 ml; 6.4 mmol) and sodium hydride (60%; 384 g; 9.6 mmol) in 30 ml dry THF is refluxed overnight. The solution is cooled and 4-(benzoxazol-2-yl)benzyl bromide (1.95 g; 6.75 mmol) is added in one portion and refluxing continued for 5 hrs. The solution is quenched with the addition of 2 ml H2O, concentrated in vacuo poured into H2O and extracted with 2×100 ml CH2Cl2, dried (Na2SO4), concentrated in vacuo and flash chromatographed using 9:1 6:1; hexane:EtOAc to obtain 3-[3-(benzoxazol-2-yl)benzyloxy]cyclohexane which is used directly in the next step.

Workup

  1. temperatureis refluxed overnight
  2. temperatureThe solution is cooled
  3. temperaturerefluxing
  4. customThe solution is quenched with the addition of 2 ml H2O
  5. concentrationconcentrated in vacuo
  6. additionpoured into H2O
  7. extractionextracted with 2×100 ml CH2Cl2
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo and flash
  10. customchromatographed

Sources & evidence

ORD record
ord-c8ab0d06efd542cea6fbd5bd158661ed
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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