Dimethylformamide → 2-Chloro-5-hydroxycyclohex-1-enecarbaldehyde

HRID 629607Notes

Reaction equation

HRID 629607 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[Si]([O:18][CH:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(C(C)(C)C)(C)C>C(OCC)(=O)C>[Cl:3][C:22]1[CH2:23][CH2:24][CH:19]([OH:18])[CH2:20][C:21]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 866425022-Chloro-5-hydroxycyclohex-1-enecarbaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (4.08 mL) was added to cooled (−10° C.) N,N-dimethylformamide (20 mL). The temperature was maintained below 0° C. Stirring was continued for another 30 minutes before the addition of 4-(tert-butyldimethylsilyloxy)cyclohexanone (10 g). The mixture was then stirred at room temperature for 2 hours before it was diluted with ethyl acetate (300 mL) and washed with water (3×), brine and dried over Na2SO4. After filtration and concentration, the crude product was used directly in the next reaction without further purification.

Workup

  1. temperatureThe temperature was maintained below 0° C
  2. stirringThe mixture was then stirred at room temperature for 2 hours before it
  3. washwashed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was used directly in the next reaction without further purification

Sources & evidence

ORD record
ord-a75b6494b7114797a90970a55f34efd2
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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