Pyridine → HCID 18688956, compound

HRID 1871826Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].N1C=CC=CC=1.[C:26](Cl)(=[O:30])[C:27]([CH3:29])=[CH2:28]>O1CCCC1>[C:26]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:30])[C:27]([CH3:29])=[CH2:28]

Participants

Conditions

Temperature: 0 °C

Procedure

16-Hydroxyhexadecanoic acid (6.81 g, 25.0 mmol) was dissolved in tetrahydrofuran (150 ml) and the solution was cooled to 0° C. before adding pyridine (2.73 g, 34.5 mmol). Methacryloyl chloride (2.61 g, 25.0 mmol) was dissolved in tetrahydrofuran (75 ml) and added dropwise. The mixture was stirred for 1 hour at 0° C., and then at room temperature for 24 hours. The solvent was removed under reduced pressure (room temperature), the residue suspended in either (100 ml) and the mixture washed with distilled water. The ether layer was dried (MgSO4) and the ether evaporated. Chromatographic purification on a silica gel column (1:2 ethyl acetate/hexane) afforded 5.0 g (64%) of the title compound. 1H NMR (60 MHz, CDCl3), δ 1.3 (br s, 26H, (CH2)13), 1.95 (m, 3H, C=CCH3), 2.1-2.6 (m, 2H, CH2COO ), 4.9-4.4 (m, 2H, COOCH2), 5.52 (m, 1H, vinyl), 6.10 (M, 1H, vinyl).

Workup

additionadded dropwise
waitat room temperature for 24 hours
customThe solvent was removed under reduced pressure (room temperature)
washthe mixture washed with distilled water
dry with materialThe ether layer was dried (MgSO4)
customthe ether evaporated
customChromatographic purification on a silica gel column (1:2 ethyl acetate/hexane)

Sources & evidence

ORD record: ord-06746133afe242e19f3423d5365039d0
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06106806

Reaction notes

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