Pyridine → HCID 18688956, compound

HRID 1734969Notes

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 ether (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): δ1.3 (br s, 26H, (CH2)13), 1.95 (m, 3H, C=CCH3), 2.1-2.6 (m, 2H, CH2COO), 4.0-4.4 (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-a0b09fcd44ec4ff1a8b64561c03a23e8
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536490

Reaction notes

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