Water → HCID 22340242, compound

HRID 585168Notes

Reaction equation

HRID 585168 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1([CH2:17][C:18]#[CH:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[OH2:20]>CO>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1([CH2:17][C:18](=[O:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 962WaterHCID 20823305HCID 20823305, compound

Product 1

HCID 22340242HCID 22340242, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

45 g (0.123 moles) of the compound having formula (XIV) obtained as described in the previous step (b), dissolved in 50 ml of methanol, are added to the suspension thus obtained. The reaction mixture is then left under stirring at room temperature for 18 hours and is subsequently hydrolyzed with water and extracted with various portions of ethyl ether. The ether extracts are joined, anhydrified on Na2SO4 and concentrated by evaporation at reduced pressure, obtaining at the end an oily red residue containing 43.5 g of the desired product having formula (XV) (65% purity upon GC analysis, 86% yield). Analyses show that both ethyl ester (45%) and methyl ester (55%) deriving from the transesterification of the product (XV) due to the use of methanol as solvent, are present. The product is not additionally purified.

Workup

  1. customobtained
  2. additionare added to the suspension
  3. customthus obtained
  4. waitThe reaction mixture is then left
  5. extractionextracted with various portions of ethyl ether
  6. concentrationconcentrated by evaporation at reduced pressure
  7. customobtaining at the end an oily red residue

Sources & evidence

ORD record
ord-a476f36ce8db471791f13246e0f9da6a
Source dataset
uspto-grants-2005_08
Patent number
US06930158B2

Reaction notes

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