HCID 86665239, compound → HCID 49802853, compound

HRID 1028087Notes

Reaction equation

[CH2:1]([O:19][CH:20]([CH2:28][CH3:29])[C:21]([O:23]C(C)(C)C)=[O:22])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18]>C(O)=O.C(OCC)C>[CH2:1]([O:19][CH:20]([CH2:28][CH3:29])[C:21]([OH:23])=[O:22])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of tert-butyl 2-((3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaen-1-yloxy)butanoate (2.09 g, 4.58 mmol) in HCOOH (9 mL) was stirred at 40° C. under N2-atmosphere for 6 hrs. The reaction mixture was diluted with diethyl ether (100 mL), washed with water (30 mL), dried (MgSO4), filtered and evaporated under reduced pressure. Dry-flash on silica gel (50 g) eluting with toluene-toluene/EtOAc (85:15) yielded 1.44 g of the crude title compound. Flash chromatography on silica gel (30 g) eluting with heptane-heptane/(EtOAc w/5% HCCOH) 98:2-95:5-80:20 yielded 1.07 g (58% yield) of the title compound as a liquid. 1H NMR (200 MHz, CDCl3) δ 0.97 (t, 3H), 0.99 (t, 3H), 1.75-1.91 (m, 2H), 2.00-2.15 (m, 2H), 2.35-2.48 (m, 2H), 2.78-2.87 (m, 8H), 3.47-3.62 (m, 2H), 3.86 (dd, 1H), 5.25-5.55 (m, 10H). MS (electrospray) (neg): 345 (M−H)−.

Workup

washwashed with water (30 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure
washDry-flash on silica gel (50 g) eluting with toluene-toluene/EtOAc (85:15)
customyielded 1.44 g of the crude title compound
washFlash chromatography on silica gel (30 g) eluting with heptane-heptane/(EtOAc w/5% HCCOH) 98:2-95:5-80:20

Sources & evidence

ORD record: ord-37d20da0914f4c0da09a37aef3d14f87
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735436B2

Reaction notes

Loading…