Diethyl Ether → HCID 53767454, compound

HRID 1155965Notes

Reaction equation

HRID 1155965 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=1[C:15]([CH3:19])([CH3:18])[CH2:16][OH:17].C(N([CH2:25][CH3:26])CC)C.[CH2:27]([O:29]CC)C>>[C:1]([O:17][CH2:16][C:15]([C:8]1[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:7]=1[O:6][C:27](=[O:29])[CH2:25][CH3:26])([CH3:19])[CH3:18])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 20536186HCID 20536186, compound

Product 1

HCID 53767454HCID 53767454, compound

Procedure

Propionyl chloride (5.1 g) was added dropwise to 2-(2-hydroxy-5-cyanophenyl)-2-methyl-1-propanol (5 g) prepared as in Example 26 and triethylamine (5.5 g) in diethyl ether (50 ml) with stirring and cooling. After stirring for 3 hours at room temperature, the mixture was washed twice with water, dried over magnesium sulphate and run down, giving 6.5 g of crude product. After filtration through alumina in toluene, 5.3 g of title product were obtained as a viscous oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 3 hours at room temperature
  3. washthe mixture was washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. customgiving 6.5 g of crude product
  6. filtrationAfter filtration through alumina in toluene

Sources & evidence

ORD record
ord-84ee9daaada844119230d97efc2b2e15
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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