Water → HCID 25010671, compound

HRID 1925674Notes

Reaction equation

[CH3:1]/[C:2](=[CH:8]\[CH:9]=[CH:10]\[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25])/[C:3]([O:5]CC)=[O:4].[OH-].[K+].O>CO>[CH3:1]/[C:2](=[CH:8]\[CH:9]=[CH:10]\[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25])/[C:3]([OH:5])=[O:4]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of ethyl (2E,4E,8Z,11Z,14Z,17Z)-2-methyl-icosa-2,4,8,11,14,17-hexaenoate (10) in methanol was added an aqueous solution of KOH (8 equiv.) and the mixture was heated to 60-70° C. for 2 hrs. The solution was cooled, water was added and the mixture acidified. The mixture was then extracted with ethyl acetate. The combined organic phases were washed with water and dried (MgSO4). Evaporation of the solvents under reduced pressure followed by flash chromatography on silica gel (8:2 hexane-EtOAc) gave the acid 11. δH(300 MHz): 0.96 (t, J 7.5, 3H, CH3), 1.91 (d, J 0.75, 3H, CH3), 2.08 (m, 2H), 2.2-2.4 (m, 4H), 2.7-2.9 (m, 6H), 5.2-5.5 (m, 8H), 6.11 (dt, J 15.0, J 6.5, 1H), 6.37 (dd, J 15.0, J 11.3, 1H), 7.26 (br d, J 11.3, 1H); δc(75 MHz) 12.16, 14.24, 20.53, 25.52, 25.61, 25.67, 26.57, 33.24, 124.44, 126.34, 126.97, 127.82, 128.04, 128.21, 128.54, 128.70, 128.74, 132.01, 140.79, 143.47, 174.28.

Workup

temperatureThe solution was cooled
extractionThe mixture was then extracted with ethyl acetate
washThe combined organic phases were washed with water
dry with materialdried (MgSO4)
customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record: ord-dab36afef2d8447bab8abc1257fc9898
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178708B2

Reaction notes

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