Hydrochloric Acid → 3-Isobutyryl-1,8-dioxaspiro[4.5]decan-2-one

HRID 1747706Notes

Reaction equation

HRID 1747706 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 667618043-Isobutyryl-1,8-dioxaspiro[4.5]decan-2-one

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-435864939e834f2c983329752c6145a6
Source dataset
uspto-grants-2015_10
Patent number
US09150583B2

Reaction notes

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