Sodium hydride → HCID 85982055, compound

HRID 2250632Notes

Reaction equation

HRID 2250632 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[CH2:10][CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1>CN(C=O)C>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[O:12][CH2:11][CH2:10][O:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 85982055HCID 85982055, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 60% NaH (2.66 g) in DMF (20 mL) was added methyl hydroxyacetate (5.00 g) under ice-water cooling, and the mixture was stirred at 0° C. for 0.5 hour. To this was added 2-(2-bromoethoxy)tetrahydro-2H-pyran (12.8 g) under ice-water cooling, and the mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between AcOEt and water. The organic layer was separated, washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (10:1-3:1) to give methyl [2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]acetate pale yellow oil (445 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customThe mixture was partitioned between AcOEt and water
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a mixture of hexane and AcOEt (10:1-3:1)

Sources & evidence

ORD record
ord-ed6f139b05da4a6aa8a8d0149bf3d798
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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