Bromoacetic Acid → HCID 20612478, compound

HRID 2202931Notes

Reaction equation

HRID 2202931 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].Br[CH2:10][C:11]([OH:13])=[O:12]>C1COCC1>[CH3:3][C:4]([CH3:8])([CH3:7])[CH2:5][O:6][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 6404Neopentyl alcoholHCID 24758Sodium hydride

Product 1

HCID 20612478HCID 20612478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (40% oil dispersion, 432 mg) was added to a solution of 2,2-dimethylpropan-1-ol (0.319 ml) in THF (15 ml) at 0° C. After stirring for 5 min, 2-bromoacetic acid (500 mg) was added. The mixture was refluxed under Ar atmosphere for 2 h. The mixture was quenched with water, washed with EtOAc, acidified with 1 M HCl (11 ml) and extracted with EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo to give the title compound (490 mg) as a pale pink oil.

Workup

  1. temperatureThe mixture was refluxed under Ar atmosphere for 2 h
  2. customThe mixture was quenched with water
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e76754805da84fd38975587940c6a504
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…