2-Methyl-2-butene → HCID 11196453, Verbindung

A solution of (E)-4-oxohexadec-2-enal (400 mg, 1.58 mmol) and 2-methyl-2-butene (1.69 ml, 15.8 mmol) in t-BuOH (20 ml) was treated with NaH2PO4 (2.00 g, 16.7 mmol) and NaClO2 (181 mg, purity 80%, 1.89 mmol), both dissolved in H2O (10 ml), and the resulting mixture was stirred for 2 h at RT. Most of the solvent was removed under reduced pressure, and EtOAc (50 ml) and a saturated NaCl solution (10 ml) were added to the residue. The aqueous phase was acidified to a pH of 1 by dropwise addition of 1 N HCl. The organic phase was then separated off and the aqueous phase was extracted with EtOAC (2×50 ml). The combined organic phases were dried over NaSO4 and concentrated under reduced pressure to give the product as a whitish-yellow solid (350 mg, 1.31 mmol, 83%), melting point 98±0.5° C. 1H NMR (400 MHz, CD3CD2OD) δ 1H ppm: 0.87 (t, 3H, J=7.0 Hz, H-16), 1.08-1.34 (m, 18H), 1.56-1.63 (m, 2H), 2.68 (t, 2H, J=7.0 Hz, H-5), 6.65 (d, 1H, J=16.2 Hz, H-2), 7.01 (d, 1H, J=16.2 Hz, H-3); 13C NMR (100.5 MHz, CD3CD2OD) δ 13C ppm: 15.5 (C-16), 24.6, 25.7, 26.2, 31.0, 31.3, 31.4, 31.5, 31.6, 31.6, 33.9, 43.0 (C-5), 133.7 (C-2), 141.3 (C-3), 169.4 (C-1), 202.8 (C-4); (−)-ESI-CID-MS: m/z 267 [M−H]−, 535 [2M−H]−; (−)-ESI-CID-MS: m/z 269 [M−H]; ESI-FT-ICR-MS: m/z 267.19633 (calculated for C16H27O3−, m/z 267.19633).

1. customMost of the solvent was removed under reduced pressure, and EtOAc (50 ml)
2. additiona saturated NaCl solution (10 ml) were added to the residue
3. additionThe aqueous phase was acidified to a pH of 1 by dropwise addition of 1 N HCl
4. customThe organic phase was then separated off
5. extractionthe aqueous phase was extracted with EtOAC (2×50 ml)
6. dry with materialThe combined organic phases were dried over NaSO4
7. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-e4590f1fdf4b4d47996cd28ff5404613

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08648115B2