tert-Butanol → 4-Tert-butoxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

HRID 225352Notes

Reaction equation

HRID 225352 reaction equation
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1.[C:19]([OH:23])([CH3:22])([CH3:21])[CH3:20].OC1CC(=O)C(CCCCCCC(OCC)=O)=C1>C(=O)([O-])[O-].[Ag+2].CO>[C:19]([O:23][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 98379417-(3-Hydroxy-5-oxo-1-cyclopentenyl)-heptanoic acid ethyl esterHCID 204655494-Bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one

Product 1

HCID 233299924-Tert-butoxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 6.35 g. (20 mmoles) of 4-bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one (Example 9), 3.01 g. (11 moles) of silver carbonate, and 40 ml. of t-butanol is heated at 70° C. for 17 hours. The mixture is cooled and filtered. After evaporation of t-butanol the residue is treated with aqueous sodium chloride and extracted with 3:1 ether-hexane. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is purified by chromatography on silica gel to give in order of elution: the subject compound as an oil; λmax.MeOH =219 mμ (8860); νmax.=1735 (ester carbonyl group), 1725 (ketone carbonyl group), and 1365 cm-1 (tert.-butyl group); and 4-hydroxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one also as an oil.

Workup

  1. additionA stirred mixture of 6.35 g
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customAfter evaporation of t-butanol the residue
  5. additionis treated with aqueous sodium chloride
  6. extractionextracted with 3:1 ether-hexane
  7. washThe extract is washed with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe crude product is purified by chromatography on silica gel
  11. customto give in order of elution

Sources & evidence

ORD record
ord-aba8f5f93dfc40cd9ea04c0b4faeb07d
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Reaction notes

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