Retinol → HCID 86759984, compound

HRID 1796880Notes

Reaction equation

Cl.C(N=C=N[CH2:7][CH2:8][CH2:9]N(C)C)C.[CH3:13][C:14]1[CH2:19][CH2:18][CH2:17][C:16]([CH3:21])([CH3:20])[C:15]=1/[CH:22]=[CH:23]/[C:24](/[CH3:33])=[CH:25]/[CH:26]=[CH:27]/[C:28](/[CH3:32])=[CH:29]/[CH2:30][OH:31]>C(Cl)Cl>[C:30]([O:31][CH2:30]/[CH:29]=[C:28](\[CH3:32])/[CH:27]=[CH:26]/[CH:25]=[C:24](\[CH3:33])/[CH:23]=[CH:22]/[C:15]1[C:16]([CH3:20])([CH3:21])[CH2:17][CH2:18][CH2:19][C:14]=1[CH3:13])(=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]/[CH:22]=[CH:15]\[CH:14]=[CH:19]\[CH2:18][CH2:17][CH2:16][CH2:9][CH2:8][CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride [EDCI] (0.71 g, 3.67 mmol) and anhydrous methylene chloride 15 ml were added to nitrogen filled, three mouth- round bottom flask and melted. The reaction mixture was cooled down into 0° C. Conjugated linoleic acid was added, and stirred for approximately 30 minutes. Retinol (0.87 g, 3.05 mmol) and N,N′-dimethylaminopyridine (DMAP) solubilized in anhydrous methylene chloride 7 ml were added into the reaction mixture, and stirred for 4 hours at room temperature. Organic phase were washed with water (20 ml×2) and brine (20 ml×2) and dried with anhydrous MgSO4, concentrated under low pressure and separated with column chromatography (solvent:ethylacetate/hexane=1/8).

Workup

additionfilled
additionwere added into the reaction mixture
stirringstirred for 4 hours at room temperature
washOrganic phase were washed with water (20 ml×2) and brine (20 ml×2)
dry with materialdried with anhydrous MgSO4
concentrationconcentrated under low pressure
customseparated with column chromatography (solvent:ethylacetate/hexane=1/8)

Sources & evidence

ORD record: ord-6195c2051e1a441f86ec18b56176a3cc
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030265B2

Reaction notes

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