Triethylamine → HCID 54522510, compound

HRID 1359156Notes

Reaction equation

HRID 1359156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([OH:10])=[O:9].[C:16]([O:21][CH2:22]Cl)(=[O:20])[CH2:17][CH2:18][CH3:19].C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[C:16]([O:21][CH2:22][O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 168483',4'-Dimethoxycinnamic acidHCID 2725008Chloromethyl butanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 54522510HCID 54522510, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3,4-dimethoxycinnamic acid (5 g, 24 mmol) and chloromethyl butyrate (3.3 g, 1 eq.) in dry dimethylformamide (20 mL), under nitrogen was dropwise added triethylamine (4 mL, 2.3 g, 1.2 eq). The reaction mixture was heated to 70° C. overnight; during that time a large amount of precipitate formed and TLC (ethyl acetate:hexane 1:2) showed that all the acid had reacted. The precipitate was filtered and washed with ethyl acetate. The filtrate was partitioned between water and ethyl acetate. The aqueous phase was washed with a small amount of ethyl acetate, and the combined organic phase was washed with water (3×), 5% solution of NaHCO3 (2×), and brine (2×), dried with MgSO4 and evaporated to give crude product as a yellow heavy oil (5.7 g). The crude product was chromatographed on silica gel (200 g, ethyl acetate:hexane 1:3) to give the pure product (second fraction) as a colorless oil (4.7 g, 64% yield).

Workup

  1. customduring that time a large amount of precipitate formed
  2. customhad reacted
  3. filtrationThe precipitate was filtered
  4. washwashed with ethyl acetate
  5. customThe filtrate was partitioned between water and ethyl acetate
  6. washThe aqueous phase was washed with a small amount of ethyl acetate
  7. washthe combined organic phase was washed with water (3×), 5% solution of NaHCO3 (2×), and brine (2×)
  8. dry with materialdried with MgSO4
  9. customevaporated
  10. customto give crude product as a yellow heavy oil (5.7 g)
  11. customThe crude product was chromatographed on silica gel (200 g, ethyl acetate:hexane 1:3)

Sources & evidence

ORD record
ord-f2cf1c477b8c4b61b43c076f916dfcd9
Source dataset
uspto-grants-2003_07
Patent number
US06599937B1

Reaction notes

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