HCID 86665237, compound → HCID 49787416, compound

HRID 1053547Notes

Reaction equation

HRID 1053547 reaction equation
[CH2:1]([C:3]([O:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH3:33])([CH2:11][CH3:12])[C:4]([O:6]C(C)(C)C)=[O:5])[CH3:2]>C(O)=O>[CH2:1]([C:3]([O:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH3:33])([CH2:11][CH3:12])[C:4]([OH:6])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 86665237HCID 86665237, compound

Product 1

HCID 49787416HCID 49787416, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of formic acid (5 ml) and tert-butyl 2-ethyl-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-yloxy)butanoate (250 mg, 0.55 mmol) was stirred vigorously under nitrogen at room temperature for 4.5 hours. The formic acid was removed in vacuo. The residue was purified by flash chromatography on silica gel using increasingly polar mixtures of heptane and ethyl acetate (100:0→80:20) as eluent. Concentration of the appropriate fractions afforded 163 mg (74% yield) of the title compound as an oil. 1H NMR (300 MHz, CDCl3): δ 0.86 (t, 6H), 0.99 (t, 3H), 1.36-1.57 (m, 2H), 1.68 (dd, 2H), 1.73-1.98 (m, 4H), 2.11 (tt, 4H), 2.70-3.01 (m, 8H), 3.39 (t, 2H), 5.20-5.56 (m, 10H). MS (electrospray): 481.4 [M+Na]+.

Workup

  1. customThe formic acid was removed in vacuo
  2. customThe residue was purified by flash chromatography on silica gel using
  3. temperatureincreasingly polar mixtures of heptane and ethyl acetate (100:0→80:20) as eluent

Sources & evidence

ORD record
ord-3468ced0cb824bab871db3bbfc7e5f9f
Source dataset
uspto-grants-2016_07
Patent number
US09394228B2

Reaction notes

Loading…