Formaldehyde → HCID 67256194, compound

HRID 1752017Notes

Reaction equation

HRID 1752017 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=[O:4].[C:19](=[O:22])([O-])[O-].[K+].[K+].C=O.C1C[O:30][CH2:29]C1>O>[CH3:1][O:2][C:3]([C:5]1([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[CH2:9][CH2:8][C:7]([CH2:19][OH:22])([CH2:29][OH:30])[C:6]1=[O:10])=[O:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 4204026HCID 4204026, compound

Product 1

HCID 67256194HCID 67256194, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(4-Chlorobenzyl)-2-oxo-cyclopentancarboxylic acid methyl ester (Compound No. (XXV)-1, (Compound (XXV), R2=CH3, Ym=4-Cl, A=N) (266.7 mg, 1.00 mmol) was combined with potassium carbonate (69 mg, 0.50 mmol), 37% aqueous solution of formaldehyde (0.242 ml, 3.00 mmol) and THF (0.72 ml) and vigorous stirring was conducted at room temperature for 5 hours. After completion of the reaction, water was added and extraction with ethyl acetate was conducted. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance.

Workup

  1. additionwas added
  2. extractionextraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away
  6. customThe residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification
  7. customto obtain the desired substance

Sources & evidence

ORD record
ord-3ba1409c68934ba589336d6cedbd0de6
Source dataset
uspto-grants-2015_10
Patent number
US09162966B2

Reaction notes

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