Water → (E,E,E)-7-benzylcarbamoyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol

HRID 26984Notes

Reaction equation

[C:1](/[C:4](/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:5]/[CH2:6][CH2:7]/[C:8](/[CH3:12])=[CH:9]/[CH2:10][OH:11])([OH:3])=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.O>ClCCl>[CH2:39]([NH:46][C:1](/[C:4](/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:5]/[CH2:6][CH2:7]/[C:8](/[CH3:12])=[CH:9]/[CH2:10][OH:11])=[O:3])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 0 °C

Procedure

660 mg of (E,Z,E) and (E,E,E)-7-carboxy-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol was dissolved in 10 ml of dichloromethane. The solution was cooled to 0° C., 440 mg of dicyclohexylcarbodiimide was added and the mixture was stirred for 1 hour. Then, 0.5 ml of benzylamine was added and stirring was continued for 1 hour. The reaction mixture was left at room temperature overnight and water was added followed by extraction with ethyl ether. The oily substance derived from the extract was purified by a thin-layer chromatography to afford 315 mg of the end product.

Workup

stirringstirring
waitwas continued for 1 hour
waitThe reaction mixture was left at room temperature overnight
extractionfollowed by extraction with ethyl ether
customwas purified by a thin-layer chromatography

Sources & evidence

ORD record: ord-a8de6253850c4925a56629f468c6d42d
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151357

Reaction notes

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