HCID 13343708, compound → HCID 13343710, compound

HRID 1154591Notes

Reaction equation

HRID 1154591 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7](O)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:22][CH3:23].[H][H]>S(=O)(=O)(O)O.[Pd].C(O)(=O)C>[Cl:1][C:2]1[C:10]2[O:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:22][CH3:23]

Participants

6

Reactant 2

HCID 13343708HCID 13343708, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13343710HCID 13343710, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (15h) (2.67 g., 0.008 mol) and 3 drops of concentrated sulfuric acid in 100 ml. of glacial acetic acid was treated with 0.3 g. of 20% palladium on carbon in a Parr apparatus under 3 atmospheres of hydrogen for 2 hours at room temperature. The solvent was evaporated under reduced pressure and the residue was dissolved in chloroform. This solution was washed with aqueous sodium bicarbonate and brine solutions, dried over anhydrous sodium sulfate, and evaporated. There resulted an 82.5% yield of diethyl 7-chloro-2,3-dihydro-6-methoxybenzofuran-2,2-dicarboxylate, m.p. 97°-99° C. Analysis (C15H17ClO6) C,H.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThis solution was washed with aqueous sodium bicarbonate and brine solutions
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-384b059eef9c41869812ff0d6e950f6a
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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