Formic Acid → HCID 49802852, compound

HRID 1028085Notes

Reaction equation

[CH2:1]([O:23][CH:24]([CH3:32])[C:25]([O:27]C(C)(C)C)=[O:26])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].[CH:33](O)=O>C(OCC)C>[CH2:1]([O:23][CH:24]([CH2:32][CH3:33])[C:25]([OH:27])=[O:26])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of tert-butyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaen-1-yloxy)propanoate (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 (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), 1.64-1.91 (m, 4H), 2.00-2.23 (m, 4H), 2.78-2.87 (m, 10H), 3.42-3.66 (m, 2H), 3.85 (dd, 1H), 5.26-5.46 (m, 12H). MS (electrospray) (neg): 399 (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 (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-700f432dedce41e49fb55a7b9d954594
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735436B2

Reaction notes

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