Pyridine → 4-(Tetradecanoyloxy)methyl-4-vinyltetrahydro-2-furanone

HRID 363501Notes

Reaction equation

HRID 363501 reaction equation
[OH:1][CH2:2][C:3]1([CH:9]=[CH2:10])[CH2:7][O:6][C:5](=[O:8])[CH2:4]1.N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[C:26](Cl)(=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C(Cl)Cl>[C:26]([O:1][CH2:2][C:3]1([CH:9]=[CH2:10])[CH2:7][O:6][C:5](=[O:8])[CH2:4]1)(=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 66986Myristoyl chlorideHCID 105587194-Hydroxymethyl-4-vinyltetrahydro-2-furanone

Product 1

HCID 105941764-(Tetradecanoyloxy)methyl-4-vinyltetrahydro-2-furanoneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8b (0.2 g, 1.4 mmol) in CH2Cl2 (20 mL) was treated with pyridine (0.45 mL, 5.6 mmol), dimethylaminopyridine (0.034 g, 0.28 mmol), and tetradecanoyl chloride (0.76 mL, 2.8 mmol). After stirring for 2 h at room temperature, the reaction mixture was concentrated, and residue was purified by flash column chromatography over silica gel with hexane:EtOAc (3:1) as eluant to give 8c (0.49 g, 99%) as an oil: IR (neat) 1788 and 1741 cm-1 (C=O); 1H NMR (CDCl3) δ 0.86 (distorted t, 3 H, CH3), 1.25 (m, 20 H, CH3 (CH2)10CH2CH2CO), 1.60 (m, 2 H, CH3 (CH2)10CH2CH2CO), 2.31 (t, J=7.4 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.60 (s, 2 H, H-3), 4.12 (AB q, J=11.3 Hz, 2 H, CH2OCOC13H27), 4.20 (AB q, J=9.3 Hz, 2 H, H-5), 5.19 (d, J=17.6 Hz, 1 H, CH=CHH), 5.28 (d, J=10.9 Hz, 1 H, CH=CHH), 5.84 (dd, J=10.9, 17.6 Hz, CH=CH2), 13C NMR (CDCl3) δ 14.02, 22.58, 24.69, 28.99, 29.11, 29.24, 29.34, 29.48, 29.53, 29.56, 31.81, 33.93, 36.57, 45.76, 66.63, 73.60, 116.63, 136.81, 173.27, 175.03. Anal. Calcd for C21H36O4 : C, 71.55; H: 10.30. Found. C, 71.46; H, 10.30.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customresidue was purified by flash column chromatography over silica gel with hexane:EtOAc (3:1) as eluant

Sources & evidence

ORD record
ord-22e40f2cdadc4e5bb32d445033f2f5ba
Source dataset
uspto-grants-1999_02
Patent number
US05874464

Reaction notes

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