Formaldehyde → HCID 89767917, compound

HRID 591548Notes

Reaction equation

HRID 591548 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[CH:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:8]=2[CH:7]=1.[CH2:24]=[O:25].C[O-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([CH2:24][OH:25])([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10942334Sodium MethoxideHCID 89767875HCID 89767875, compound

Product 1

HCID 89767917HCID 89767917, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of methyl 6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-carboxylate (400 mg) and DMSO (11 mL) were added paraformaldehyde (37.4 mg) and sodium methoxide (6.8 mg). The mixture was stirred at room temperature for 2 h. The mixture was quenched with water and 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (332.6 mg).

Workup

  1. customThe mixture was quenched with water and 1N HCl at 0° C.
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-0a72c462ed9f4af28281fd8adfb7a8fc
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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