Sodium hydride → HCID 69205132, compound

HRID 2252368Notes

Reaction equation

HRID 2252368 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][OH:13])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:16]1)[O:11][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 980723-(Benzyloxy)-1,2-propanediolHCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

Product 1

HCID 69205132HCID 69205132, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution, 0° C., of 1-benzylglycerol (3.00 g) in dimethylformamide (165 ml) was added sodium hydride (60% dispersion in mineral oil, 3.95 g) and the reaction stirred for 45 minutes. 1-Tetrahydropyran-2-yloxy-6-bromohexane (13.10 g) was added and the reaction stirred at 20° C. for 19 hours. The reaction was quenched by the portionwise addition of methanol(10 ml) over 30 minutes at 0° C. The solvent was removed in vacuo and the residue partitioned between water (125 ml) and dichloromethane(125 ml). The organic layer was washed with brine (150 ml), dried and the solvent removed in vacuo. This was purified by column chromatography on silica gel (Biotage) eluting with 8% ethyl acetate in cyclohexane to give the title compound as a pale yellow oil (3.74 g).

Workup

  1. stirringthe reaction stirred at 20° C. for 19 hours
  2. customThe reaction was quenched by the portionwise addition of methanol(10 ml) over 30 minutes at 0° C
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between water (125 ml) and dichloromethane(125 ml)
  5. washThe organic layer was washed with brine (150 ml)
  6. customdried
  7. customthe solvent removed in vacuo
  8. customThis was purified by column chromatography on silica gel (Biotage)
  9. washeluting with 8% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-17a4f95523c94d7fb5a908cb4a5166c2
Source dataset
uspto-grants-2008_01
Patent number
US07321059B2

Reaction notes

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