1,2-Dichloroethane → (R)-3-undecanoyloxytetradecanoic acid

HRID 277591

Reaction equation

HRID 277591 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:14](Cl)[CH2:15]Cl.CI.[CH3:20][C:21]([OH:23])=[O:22]>C(Cl)Cl.[Zn]>[C:1]([O:13][C@H:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:14][CH3:15])[CH2:20][C:21]([OH:23])=[O:22])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 6328Methyl iodideHCID 8180Undecanoic Acid

Product 1

HCID 54121365(R)-3-undecanoyloxytetradecanoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the compound prepared in Example 1-(2) (2.5 g, 5.68 mmol) was treated with undecanoic acid (1.16 g, 6.25 mmol) and EDC.MeI (2.08 g, 7.0 mmol) in CH2Cl2 (60 mL) and then deprotected as described in Example 1-(3) with zinc (9.3 g, 142 mmol) in AcOH (40 mL) to afford (R)-3-undecanoyloxytetradecanoic acid as a colorless oil: 1H NMR (CDCl3) δ 0.89 (t, 6 H, J=6.7 Hz), 1.0-1.75 (m, 44 H), 2.29 (m, 2 H), 2.61 (m, 2 H), 5.22 (m, 1 H).

Sources & evidence

ORD record
ord-80eddb78be594d4ca0182f296bdb01e2
Source dataset
uspto-grants-2002_03
Patent number
US06355257B1

Linked notes

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