Sodium hydride → HCID 11021838, compound

HRID 1518889Notes

Reaction equation

HRID 1518889 reaction equation
[H-].[Na+].[CH2:3]([OH:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:12])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 694201,8-OctanediolHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 11021838HCID 11021838, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The oil attached to 63 wt % sodium hydride (1.14 g, 30.1 mmol, 1.00 eq.) was washed three times with hexane and removed. Subsequently, thereto were added dry DMF (30.0 mL) and 1,8-octanediol (4.40 g, 30.1 mmol, 1.00 eq.) at 0 degrees. The mixture was allowed to react for 5 minutes with ice-cooling, and then thereto was dropwise added a solution of PMBCl (4.08 mL, 30.1 mmol, 1.00 eq.) in dry DMF (20.0 mL) over 1 hour. The reaction mixture was allowed to react for further 1.5 hours and then poured into an aqueous ammonium chloride solution with ice-cooling, and the organic phase was extracted with ethyl acetate. The resulting organic phase was washed with 1 M hydrochloric acid, saturated sodium bicarbonate, and a saturated salt solution. The washed organic phase was dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=75:25) to obtain 8-((4-methoxybenzyl)oxy)octa-1-nol as shown below (4.66 g, 17.5 mmol, 58%).

Workup

  1. washwas washed three times with hexane
  2. customremoved
  3. customto react for 5 minutes with ice-
  4. temperaturecooling
  5. customto react for further 1.5 hours
  6. temperaturecooling
  7. extractionthe organic phase was extracted with ethyl acetate
  8. washThe resulting organic phase was washed with 1 M hydrochloric acid, saturated sodium bicarbonate
  9. dry with materialThe washed organic phase was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=75:25)
  12. customto obtain 8-((4-methoxybenzyl)oxy)octa-1-nol

Sources & evidence

ORD record
ord-1e4849afc8f24b1eb9a45ad70da18778
Source dataset
uspto-grants-2015_07
Patent number
US09073802B2

Reaction notes

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