3-Methyl-3-pentanol → HCID 54384939, compound

HRID 1014976Notes

Reaction equation

HRID 1014976 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][C:7]([OH:12])([CH2:10][CH3:11])[CH2:8][CH3:9].C(N(CC)CC)C>ClCCl>[C:1]([O:12][C:7]([CH2:10][CH3:11])([CH3:6])[CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 64933-Methyl-3-pentanolHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 54384939HCID 54384939, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of acryloyl chloride (5.0 g, 55.2 mmol) and 3-methyl-3-pentanol (7.6 ml, 60.8 mmol) in dichloromethane, triethylamine (23 ml, 166 mmol) was added at room temperature under a nitrogen atmosphere. After stirring at room temperature for 14 hours, the reaction mixture was diluted with dichloromethane and washed with water and saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate=10:1) to give the titled compound (5.45 g, 63%) as a colorless oil.

Workup

  1. washwashed with water and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customAfter evaporation under reduced pressure
  4. customto remove the solvent
  5. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-365e1759025f46c3ab4ddbde6c6c1d4b
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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