Water → HCID 53987691, compound

HRID 263133Notes

Reaction equation

HRID 263133 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C@@H:6]([OH:9])[CH2:5][C:4]([CH3:11])([CH3:10])[C:3]=1[C:12]#[C:13][C:14]([CH3:18])=[CH:15][CH:16]=[O:17].[O:19]([CH2:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>N1C=CC=CC=1>[CH3:1][C:2]1[C:7](=[O:8])[C@@H:6]([O:9][C:27](=[O:28])[CH2:26][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:5][C:4]([CH3:10])([CH3:11])[C:3]=1[C:12]#[C:13][C:14]([CH3:18])=[CH:15][CH:16]=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 69703Phenoxyacetyl chlorideHCID 86736556HCID 86736556, compound

Product 1

HCID 53987691HCID 53987691, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

13.5 g of the ketoaldehyde of formula XII obtained in Example 20 are dissolved in 100 ml of pyridine. 10 g of phenoxyacetic acid chloride are added dropwise to the solution at 0° C. The mixture is stirred for 1 hour at 0° C. and then poured into water and extracted with diethyl ether. The ether extract is washed with 5% strength aqueous sulfuric acid and then with water. The 5-[2,6,6-trimethyl-3-oxo-4(S)-(phenoxyacetoxy)-cyclohex-1-en-1-yl]-3-methyl-penta-2-en-4-yn-1-al (XIV) isolated from the extract is further reacted as follows:

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. washis washed with 5% strength aqueous sulfuric acid

Sources & evidence

ORD record
ord-52bbec93df464e469252dc3f034b9100
Source dataset
uspto-grants-1979_05
Patent number
US04156090

Reaction notes

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