Benzyl Alcohol → 1-benzyloxy-4(S) acetyloxy-2-nonyne

HRID 867114Notes

Reaction equation

HRID 867114 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:12][C:13]#[C:14][C@@H:15]([O:21][C:22](=[O:24])[CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O.O>[CH2:1]([O:8][CH2:12][C:13]#[C:14][C@@H:15]([O:21][C:22](=[O:24])[CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 227938171-Bromo-4(S)-acetyloxy-2-nonyne

Product 1

HCID 228002521-benzyloxy-4(S) acetyloxy-2-nonyne

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl alcohol (1 molar equivalent) is added dropwise to a stirred suspension of sodium hydride (1 molar equivalent) in dry dimethylformamide maintained at 0° to 5° C. throughout the addition. The reaction mixture is allowed to warm to and then is maintained at room temperature for 1/2 hour. After cooling to 0° to 5° C., the reaction mixture is treated with 1-bromo-4(S)-acetyloxy-2-nonyne (1 molar equivalent) added dropwise over 1/2 hour. The resulting reaction mixture is stirred at ambient temperature for 2 hours and then diluted with water providing a turbid mixture which is extracted with ether. The organic extract is washed with water and saturated aqueous brine, dried over sodium sulfate and filtered. Evaporation (in vacuo at 40° to 50° C.) of the filtrate leaves an oily residue which is distilled to provide the pure title compound.

Workup

  1. temperaturemaintained at 0° to 5° C. throughout the addition
  2. temperatureto warm to and
  3. temperatureAfter cooling to 0° to 5° C.
  4. additionadded dropwise over 1/2 hour
  5. customThe resulting reaction mixture
  6. extractionis extracted with ether
  7. extractionThe organic extract
  8. washis washed with water and saturated aqueous brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customEvaporation (in vacuo at 40° to 50° C.) of the filtrate
  12. customleaves an oily residue which
  13. distillationis distilled

Sources & evidence

ORD record
ord-7a34c4e155c44c469a1d2173889d4a07
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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