Sodium hydride → HCID 85982055, compound

HRID 860488Notes

Reaction equation

HRID 860488 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>[CH3:8][O:7][C:5](=[O:6])[CH2:4][O:3][CH2:10][CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1

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 (4.45 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-0ba209e50bda44f7a42ae73ca46938a2
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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