Dimethylformamide → HCID 58052503, compound

HRID 2190187Notes

Reaction equation

HRID 2190187 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].CN(C=O)C.[H-].[Na+].Br[CH2:18][CH:19]=[CH2:20]>O>[CH2:20]([O:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 58052503HCID 58052503, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 3-hydroxy-2,2-dimethylpropanoate (5.59 g, 1 eq.) and DMF (42 ml) at 0° C. was slowly added NaH (60% in mineral oil, 1.69 g, 1 eq.). After 30 min, 3-bromoprop-1-ene (5.12 g, 1 eq.) was added. The reaction mixture was warmed to room temperature and stirred overnight. Water was carefully added. The resulting mixture was extracted with EtOAc, dried over MgSO4 and concentrated to yield a light-yellow oil to be used in the next step without purification.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto yield a light-yellow oil
  5. customto be used in the next step without purification

Sources & evidence

ORD record
ord-cb7d607c1c78438ba2dc9af9c5f3384a
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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