Hydrochloric Acid → HCID 66761804, compound

HRID 573782Notes

Reaction equation

HRID 573782 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.[CH3:9][CH:10]([CH3:18])[C:11](=[O:17])[CH2:12][C:13](OC)=[O:14].[O-]CC.[Na+].Cl>C(O)C>[C:11]([CH:12]1[CH2:2][C:3]2([CH2:4][CH2:5][O:6][CH2:7][CH2:8]2)[O:1][C:13]1=[O:14])(=[O:17])[CH:10]([CH3:18])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1604391,6-Dioxaspiro[2.5]octaneHCID 2723922Sodium ethoxideHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 66761804HCID 66761804, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

6.6 g 1,6-Dioxaspiro[2.5]octane and 8.2 ml methyl 4-methyl-3-oxopentanoate are dissolved in 30 ml ethanol, cooled to 0° C. and treated in portions with 3.9 g sodium ethoxide. After completion of the addition the mixture is warmed to room temperature and stirred for 18 hours. Then the mixture is poured in 200 ml ice water, acidified to pH 3 by addition of 1 M hydrochloric acid and extracted for three times with ethylacetate. The combined organic phases are dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50).

Workup

  1. additionAfter completion of the addition the mixture
  2. temperatureis warmed to room temperature
  3. extractionextracted for three times with ethylacetate
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. customthe solvents are evaporated in vacuo
  6. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50)

Sources & evidence

ORD record
ord-34528e89b8a24c86a44971d0834fbb33
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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