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

HRID 1047400Notes

Reaction equation

HRID 1047400 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-64f960d3283b400988bc0caacca40a57
Source dataset
uspto-grants-2013_10
Patent number
US08569453B2

Reaction notes

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