Water → HCID 86605584, compound

HRID 131290Notes

Reaction equation

HRID 131290 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH2:16].CN(C)[CH:19]=[O:20]>O1CCCC1.[Cl-].[Na+].O>[OH:16][CH2:14][C:12]1[O:11][CH:9]=[C:19]([O:20][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:1](=[O:4])[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 86605584HCID 86605584, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-hydroxy-2-(hydroxymethyl)-4H-pyranone (1 g) in N,N-dimethylformamide (20 mL) is added potassium carbonate (1.95 g) and tert-butyl bromoacetate (1.37 g) and the mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with tetrahydrofuran (10 mL), and thereto is added water and saturated brine. After stirring, the organic layer is separated and the aqueous layer is extracted with tetrahydrofuran. The organic layers are combined and washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate is concentrated and the residue is washed with diethyl ether and collected by filtration to give tert-butyl [[6-(hydroxymethyl)-4-oxo-4H-pyran-3-yl]oxy]acetate (1.49 g, yield; 88%) as a colorless powder. MS (ESI) m/z; 257 [M+H]+, M.p. 90-92° C.

Workup

  1. stirringAfter stirring
  2. customthe organic layer is separated
  3. extractionthe aqueous layer is extracted with tetrahydrofuran
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. washthe residue is washed with diethyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b1183dd145474eabab86c86a16fbd3be
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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