Methanol → 7-(3-Methoxy-5-oxocyclopent-1-EN-1-YL)heptanoic acid

HRID 461260

Reaction equation

HRID 461260 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]([OH:16])=[O:15])=[CH:3]1.N1C(C)=CC=CC=1C.[CH3:25][OH:26]>[B-](F)(F)(F)F.[Ag+]>[CH3:25][O:26][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]([OH:16])=[O:15])=[CH:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 79372,6-LutidineHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Product 1

HCID 233300047-(3-Methoxy-5-oxocyclopent-1-EN-1-YL)heptanoic acid

Reagents, catalysts & solvents 1

HCID 159722Silver tetrafluoroborateCatalyst

Procedure

To a stirred solution of 5.30 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 93) in 85 ml. of methanol at 0°-3° C. is added 4.40 g. (22.6 mmole) of silver fluoborate in one portion. After 2 minutes, the mixture is treated with 2.66 g. (24.8 mmoles) of 2,6-lutidine. After stirring for 30 minutes at 0°-3° C. the mixture is stirred at ambient temperature for 45 minutes. Silver bromide is removed by filtration, and the filtrate is concentrated to a volume of 40 ml. The solution is treated with saturated sodium chloride solution and extracted with ether. The extract is washed successively with 0.5N hydrochloric acid solution, water, and saturated sodium chloride solution; dried over magnesium sulfate; and concentrated. Partition chromatography of the residue on Celite gives an oil, λ maxMeOH. = 220 mμ (7450); ν max - 1715 (carbonyl groups) and 1095 cm-1 (methoxy group).

Workup

  1. additionthe mixture is treated with 2.66 g
  2. stirringis stirred at ambient temperature for 45 minutes
  3. customSilver bromide is removed by filtration
  4. concentrationthe filtrate is concentrated to a volume of 40 ml
  5. additionThe solution is treated with saturated sodium chloride solution
  6. extractionextracted with ether
  7. washThe extract is washed successively with 0.5N hydrochloric acid solution, water, and saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationand concentrated
  10. customPartition chromatography of the residue on Celite
  11. customgives an oil, λ maxMeOH

Sources & evidence

ORD record
ord-ef54f193d2174bdeab23677e56e0f83d
Source dataset
uspto-grants-1977_12
Patent number
US04061672

Linked notes

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