Triethylamine → HCID 20095715, compound

HRID 248551Notes

Reaction equation

HRID 248551 reaction equation
[CH2:1]([O:3][C:4]1(OC)[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[C:6]([C:7](O)=O)[CH:5]1[OH:16])[CH3:2].C(N(CC)CC)C.[C:26](Cl)(=O)[O:27]CC>C1COCC1>[CH2:1]([O:3][C:4]1[C:12]([O:27][CH3:26])=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[C:6]([CH3:7])[C:5]=1[OH:16])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 20095717HCID 20095717, compound

Product 1

HCID 20095715HCID 20095715, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

53 g of 3,5-diethoxy-2-hydroxy-3-methoxybenzoic acid prepared in Referential Example 5 and 45.5 g of triethylamine were dissolved in 400 ml of THF, and 48.4 g of ethyl chlorocarbonate in 100 ml of THF was dropwise added thereto with ice cooling while stirring. After the completion of the dropwise addition, the formed crystals were separated by filtration and washed with 100 ml of THF. The mother liquor was combined with the wash liquid, and a 10% aqueous solution of 30.3 g of sodium borohydride was added to the resultant solution and cooled by ice while stirring. After the completion of the dropwise addition, the mixture was stirred at room temperature for one hr, neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (eluent: n-hexane :ethyl acetate=95.5) to prepare 40 g of the product compound as a colorless oleaginous substance.

Workup

  1. additionAfter the completion of the dropwise addition
  2. customthe formed crystals were separated by filtration
  3. washwashed with 100 ml of THF
  4. additiona 10% aqueous solution of 30.3 g of sodium borohydride was added to the resultant solution
  5. temperaturecooled by ice
  6. stirringwhile stirring
  7. additionAfter the completion of the dropwise addition
  8. stirringthe mixture was stirred at room temperature for one hr
  9. extractionextracted with ethyl acetate
  10. washThe organic phase was washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated
  13. customThe concentrate was purified by silica gel column chromatography (eluent: n-hexane :ethyl acetate=95.5)
  14. customto prepare 40 g of the product compound as a colorless oleaginous substance

Sources & evidence

ORD record
ord-1baae9a5c538468fbaadd307d32c7157
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Reaction notes

Loading…