Formaldehyde → HCID 71721691, compound

HRID 591542Notes

Reaction equation

HRID 591542 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.[H-].[Na+].C=[O:27]>CN(C=O)C>[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]([OH:27])([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 89767875HCID 89767875, compound

Product 1

HCID 71721691HCID 71721691, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-carboxylate (120 mg) in DMF (dry) (3.4 mL) was added sodium hydride (15.0 mg) at 0° C. After stirring for 30 min, to the mixture was added paraformaldehyde (20.4 mg) at 0° C. The mixture was stirred at room temperature under nitrogen atmosphere for 2 h. The mixture was quenched with saturated aqueous NH4Cl 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 (12.4 mg).

Workup

  1. stirringThe mixture was stirred at room temperature under nitrogen atmosphere for 2 h
  2. customThe mixture was quenched with saturated aqueous NH4Cl at 0° C.
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed successively with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-6d1aba7d36dc423da3faa9061fb45014
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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