Triethylamine → HCID 22494100, compound

HRID 1816561Notes

Reaction equation

HRID 1816561 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([CH2:19][CH3:20])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH3:18])=[C:12]([CH:16]=1)[C:13](O)=[O:14])=[O:5])[CH3:2].ClC(OCC)=O.C(N(CC)CC)C>O1CCCC1>[OH:14][CH2:13][C:12]1[CH:16]=[C:8]([CH:9]=[CH:10][C:11]=1[O:17][CH3:18])[CH2:7][CH:6]([CH2:19][CH3:20])[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10891241HCID 10891241, compound

Product 1

HCID 22494100HCID 22494100, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.50 g of 5-[2-(ethoxycarbonyl)butyl]-2-methoxybenzoic acid was dissolved in 8 ml tetrahydrofuran, and 0.20 ml ethyl chloroformate and 0.29 ml triethylamine were added under ice-cooling. After the reaction solution was stirred for 10 minutes under ice-cooling, insoluble matters were filtered off. The mother liquor was ice-cooled again, and 10 L water and 136 mg sodium borohydride were added, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction product, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 0.47 g of ethyl 2-[3-(hydroxymethyl)-4-methoxybenzyl]butanoate was obtained.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationinsoluble matters were filtered off
  4. temperaturecooled again
  5. addition10 L water and 136 mg sodium borohydride were added
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. additionWater was added to the reaction product
  8. extractionby extracting with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. washfrom fractions eluted with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-5d300396c56e4ad99228689233cefb7d
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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