Triethylamine → HCID 54285998, compound
Reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]([O:17][CH2:18]Cl)(=[O:16])[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[C:12]([O:17][CH2:18][O:10][C:1](=[O:11])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)(=[O:16])[CH2:13][CH2:14][CH3:15]Participants
Conditions
- Temperature
- 70 °C
Procedure
To a stirred solution of cinnamic acid (10 g, 67 mmol) and chloromethyl butyrate (9.5 g, 1 eq) in dry dimethylformamide (25 mL) under nitrogen was dropwise added triethylamine (12 mL, 8.5 g, 1.2 eq). The reaction mixture was heated at 70° C. for 3 h; during that time a large amount of precipitate formed and TLC (ethyl acetate:hexane 1:4) showed that all the acid has 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 the crude product as an orange oil (15 g), which was distilled at 150° C./0.1-0.2 mm Hg. The pure product was obtained as a colorless oil (12 g, 72% yield).
Workup
- customduring that time a large amount of precipitate formed
- customhas reacted
- filtrationThe precipitate was filtered
- washwashed with ethyl acetate
- customThe filtrate was partitioned between water and ethyl acetate
- washThe aqueous phase was washed with a small amount of ethyl acetate
- washthe combined organic phase was washed with water (3×), 5% solution of NaHCO3 (2×) and brine (2×)
- dry with materialdried with MgSO4
- customevaporated
- customto give the crude product as an orange oil (15 g), which
- distillationwas distilled at 150° C./0.1-0.2 mm Hg
Sources & evidence
- ORD record
- ord-bbd57bc29e7941b3bc1ca63cabd16130
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06599937B1
Reaction notes
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