Ethanol → HCID 86627023, compound

HRID 907518Notes

Reaction equation

HRID 907518 reaction equation
[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[O:11])[C:7]=2I)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[O:11])[C:7]=2[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:13]=[O:14])[CH:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 66879547HCID 66879547, compound

Product 1

HCID 86627023HCID 86627023, compoundYield 63.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 120 mg 3-cyclopentyl-2-iodo-2-cyclopenten-1-one, 80 mg 3-formylphenylboronic acid and 20 mg tetrakis(triphenylphosphine)palladium was stirred at 80° C. overnight in 8 ml toluene, 4 ml ethanol and 4 ml 2 N aqueous sodium carbonate. Then the reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=2:1) to yield 70 mg of 3-cyclopentyl-2-(3-formylphenyl)-2-cyclopenten-1-one. 3-cyclopentyl-2-(3-formylphenyl)-2-cyclopenten-1-one in benzene was stirred with one drop of acetic acid and 100 mg sodium triacetoxyborohydride at 70-80° C. for 2 hours. Then the reaction mixture was poured into saturated aqueous ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=2:1) to yield 40 mg of 3-cyclopentyl-2-(3-hydroxymethylphenyl)-2-cyclopenten-1-one, which was then condensed with hydroxylamine hydrochloride according to a procedure similar to that described in STEP 4 for Example 1 to afford 20 mg of 3-cyclopentyl-2-(3-hydroxymethylphenyl)-2-cyclopenten-1-one oxime as a solid. 1H NMR (CDCl3, 300 MHz): δ 8.75 (bs, 1H), 7.40-7.29 (m, 3H), 7.12 (d, J=7.2 Hz, 1H), 4.66 (s, 2H), 2.98 (m, 1H), 2.75 (m, 2H), 2.61 (m, 2H), 1.71 (m, 4H), 1.55 (m, 4H).

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ffeec3caaa9f483eb2c256235df9832a
Source dataset
uspto-grants-2011_09
Patent number
US08013187B2

Reaction notes

Loading…