Triphenylphosphine → 2-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenone

HRID 573035

Reaktionsgleichung

Reaktionsgleichung von HRID 573035
[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][OH:65])[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O[C:67]1[CH:79]=[CH:78][C:77]2[C:76]3[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=3)[C:70](=[O:80])[C:69]=2[CH:68]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][O:65][C:67]2[CH:79]=[CH:78][C:77]3[C:76]4[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=4)[C:70](=[O:80])[C:69]=3[CH:68]=2)[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 813862-Hydroxyfluoren-9-oneHCID 866457853,4,5-Tris(octadecyloxy)cyclohexylmethyl alcohol

Produkt 1

HCID 594992172-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(3,4,5-Tris(octadecyloxy)-cyclohexyl)-methanol (82.5 mg, 89.7 μmol), 2-hydroxy-9-fluorenone (26.4 mg, 135 μmol) and triphenylphosphine (35.3 mg, 135 μmol) were dissolved in dehydrated THF (1.6 mL), DIED (27 μL, 137 μmol) was added, and the mixture was stirred for 1.5 hours. THF was evaporated, and 90% aqueous acetonitrile (10 mL) was added to the residue to allow crystallization. The crystals were filtered, and the obtained crystals were washed well with acetonitrile (10 mL) to give 2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenone (91.2 mg, 83.1 μmol, 93%).

Aufarbeitung

  1. additionDIED (27 μL, 137 μmol) was added
  2. customTHF was evaporated
  3. addition90% aqueous acetonitrile (10 mL) was added to the residue
  4. customcrystallization
  5. filtrationThe crystals were filtered
  6. washthe obtained crystals were washed well with acetonitrile (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6c43e07ebdcf4829b213a1b2d5287650
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029504B2

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