Tetrahydrofuran → ACMC-20apjz

HRID 1439103Notes

Reaction equation

HRID 1439103 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 93) 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 and 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 f (multiplet, O-methine hydrogen).

Workup

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

Sources & evidence

ORD record
ord-8383e533067f45779d81551b3bf4696b
Source dataset
uspto-grants-1977_11
Patent number
USRE029469

Reaction notes

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