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

HRID 1439101Notes

Reaction equation

HRID 1439101 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 94), 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 aq. 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; λ max.MeOH = 219 mμ (8860); ν max. = 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 aq. 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-2e453725a019400eb000f04785de487f
Source dataset
uspto-grants-1977_11
Patent number
USRE029469

Reaction notes

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