Tetrahydrofuran → ACMC-20apjz

HRID 225354

Reaction equation

HRID 225354 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.[O:17]1CCCC1>O.CCOCC.[B-](F)(F)(F)F.[Ag+]>[OH:17][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

6

Reactant 2

HCID 8028TetrahydrofuranHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Product 1

HCID 3690897ACMC-20apjz

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 56.0 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 400 ml. of tetrahydrofuran and 133 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during 25 minutes. The mixture is stirred at 0°-5° C. for 60 minutes, diluted with water and ether, and filtered. The aqueous portion of the filtrate is saturated with solid sodium chloride and extracted with additional ether. The combined organic phases are washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Column chromatography of the residue gives the subject compound as a mixture with 4-hydroxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one, NMR(CDCl3) 3.60 (multiplet, O-methylene hydrogens) and 4.60 (multiplet, O-methine hydrogen).

Workup

  1. filtrationfiltered
  2. extractionextracted with additional ether
  3. washThe combined organic phases are washed successively with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd869fdce46747399b17ca2efa36c7da
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Linked notes

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