Formaldehyde → HCID 59756938, compound

HRID 1009212Notes

Reaction equation

HRID 1009212 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:12])[CH2:5][CH2:6][S:7]2.[CH2:13]=[O:14].[C:15](=[O:18])([O-])[O-].[K+].[K+]>CO.O>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:12])[C:5]([CH2:15][OH:18])([CH2:13][OH:14])[CH2:6][S:7]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 12324928HCID 12324928, compound

Product 1

HCID 59756938HCID 59756938, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 5-methylthiochroman-4-one (1.00 g) in MeOH (20 ml) and water (4 ml) was admixed with 35% eq. formalin solution (4 ml) and potassium carbonate (100 mg). The reaction mixture was stirred at 40° C. for 2 h and then at RT for 2 h, the solvent was removed under reduced pressure and the residue was admixed with water. The aqueous solution was extracted repeatedly with EtOAc (3×50 ml), the combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. After column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc), the desired product was obtained as a white solid (697 mg, 52% of theory, m.p. 138-142° C.).

Workup

  1. waitat RT for 2 h
  2. customthe solvent was removed under reduced pressure
  3. extractionThe aqueous solution was extracted repeatedly with EtOAc (3×50 ml)
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customAfter column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-23f35f0e61a54a6fae9190624068ec30
Source dataset
uspto-grants-2011_07
Patent number
US07973072B2

Reaction notes

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