Ethyl orthoformate → HCID 11030653, compound

HRID 488066Notes

Reaction equation

HRID 488066 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([CH2:8][Cl:9])=[O:7])[CH3:2].C(OCC)(OCC)O[CH2:13][CH3:14]>S(=O)(=O)(O)O>[Cl:9][CH2:8]/[C:6](/[O:7][CH2:13][CH3:14])=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:10]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 11030653HCID 11030653, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of ethyl-4-chloroacetoacetate (5.0 g), triethyl orthoformate (4.5 g) and concentrated sulfuric acid (2 drops) was stirred at room temperature for 48 hours under a nitrogen atmosphere. The excess triethyl orthoformate was removed on a rotavap and the residue was dissolved in toluene (~20 mL) and a small amount of p-toluene sulfonic acid was added and refuxed for three hours. The mixture was diluted with ethyl acetate (~20 mL) and washed with aqueous sodium bicarbonate and brine; dried over anhydrous sodium sulphate and the solvent removed on a rotavap to obtain the title compound.

Workup

  1. customThe excess triethyl orthoformate was removed on a rotavap
  2. dissolutionthe residue was dissolved in toluene (~20 mL)
  3. additiona small amount of p-toluene sulfonic acid was added
  4. waitrefuxed for three hours
  5. additionThe mixture was diluted with ethyl acetate (~20 mL)
  6. washwashed with aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent removed on a rotavap

Sources & evidence

ORD record
ord-f107802cb1344a0d9bdfc52dd41fdd83
Source dataset
uspto-grants-1994_03
Patent number
US05298625

Reaction notes

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