2,2-Dimethoxypropane → HCID 22723505, compound

HRID 1581833Notes

Reaction equation

HRID 1581833 reaction equation
[C:1]([C:3]([CH3:10])([CH3:9])[CH:4]([OH:8])[CH2:5][CH2:6][OH:7])#[N:2].C(=O)([O-])[O-].[K+].[K+].CO[C:19](OC)([CH3:21])[CH3:20]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:3]([CH:4]1[CH2:5][CH2:6][O:7][C:19]([CH3:21])([CH3:20])[O:8]1)([CH3:10])[CH3:9])#[N:2]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 11430Potassium CarbonateHCID 22178188HCID 22178188, compound

Product 1

HCID 22723505HCID 22723505, compound

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Optically active 4-cyano-4-methyl-3-hydroxy-1-pentanol (500 mg, 3.49 mmol) was dissolved in 2,2-dimethoxypropane (5 mL) and p-toluenesulfonic acid (50 mg) was added. The mixture was stirred at room temperature for 30 min. Thereto was added a powder of potassium carbonate (100 mg) to neutralize the reaction mixture. The mixture was filtrated and concentrated under reduced pressure to give optically active 4-(1-cyano-1-methylethyl)-2,2-dimethyl-1,3-dioxane (614 mg, 3.35 mmol) (yield relative to optically active 4-cyano-4-methyl-3-hydroxy-1-pentanol: 96%).

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0542174516541ddb38ddce4f68cc2fb
Source dataset
uspto-grants-2004_05
Patent number
US06730803B2

Reaction notes

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