Undecylenic Acid → 1-Undecene, 11-fluoro-

HRID 879950

Reaction equation

HRID 879950 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]CCC.C(OCC(F)(F)[F:31])(=O)CCCCCCCCC#C.C(OCC(F)(F)F)(=O)CCCCCCCCC=C.C(O)(=O)CCCCCCCCC#C.C(O)(=O)CCCCCCCCC=C.FC(F)(F)CO.C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O.CN(C)C1C=CN=CC=1>[F:31][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

10

Procedure

Glassware used for surface modification was cleaned with organic solvents and etched overnight in basic detergent solution. Prior to use, it was rinsed with ultrapure water and dried at 120° C. 1-Hexadecene (98%, Sigma-Aldrich) was purified by column chromatography and vacuum distillation. 1-Hexadecyne was obtained by reacting 1-bromotetradecane with lithium acetylide ethylenediamine complex in dimethylsulfoxide. 11-Fluoroundec-1-ene was synthesized as described elsewhere.14 2,2,2-Trifluoroethyl undec-10-ynoate and 2,2,2-trifluoroethyl undec-10-enoate were synthesized by esterification of 10-undecynoic acid, respectively 10-undecenoic acid, with 2,2,2-trifluoroethanol using N,N′-dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. Solvents used were either of analytical grade or distilled prior to use.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-0b2f3dd8dcb24da89fa6a77c85fd4e20
Source dataset
uspto-grants-2015_03
Patent number
US08993479B2

Linked notes

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