Diethyl Ether → HCID 53939917, compound

HRID 1155966Notes

Reaction equation

HRID 1155966 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:18])=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:12]=1)#[N:6].C(N(CC)CC)C.[CH2:26]([O:28]CC)[CH3:27]>>[C:1]([O:15][CH2:14][C:13]([C:11]1[CH:12]=[C:7]([C:5]#[N:6])[CH:8]=[CH:9][C:10]=1[O:18][C:26](=[O:28])[CH3:27])([CH3:16])[CH3:17])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20536186HCID 20536186, compound

Product 1

HCID 53939917HCID 53939917, compound

Procedure

Acetyl chloride (3.5 g) in diethyl ether (10 ml) was added portionwise with swirling and ice cooling (5°-10° C.) to 2-(5-cyano-2-hydroxyphenyl)-2-methyl-1-propanol (3.8 g) prepared as in Example 26 and triethylamine (4.6 g) in diethyl ether (40 ml). The mixture was allowed to warm to room temperature, and was left for three hours before washing with water twice, drying over magnesium sulphate, and running down. The crude product (4 g) was dissolved in toluene and filtered through a bed of aluminium oxide. Removal of the toluene left the title product (2.3 g) as a colourless oil.

Workup

  1. washbefore washing with water twice
  2. dry with materialdrying over magnesium sulphate
  3. dissolutionThe crude product (4 g) was dissolved in toluene
  4. filtrationfiltered through a bed of aluminium oxide
  5. customRemoval of the toluene
  6. waitleft the title product (2.3 g) as a colourless oil

Sources & evidence

ORD record
ord-9a03687239ec4a67a82221002a0744df
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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