2-(3-Octadecyloxy-2,2-bis-octadecyloxymethyl-propoxy)-9-fluorenone → 2-(3-Octadecyloxy-2,2-bis-octadecyloxymethyl-propoxy)-9-(4-chlorophenyl)-9-fluorenol

HRID 573032Notes

Reaction equation

HRID 573032 reaction equation
[CH2:1]([O:19][CH2:20][C:21]([CH2:58][O:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])([CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[O:37])[C:26]=2[CH:25]=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].[Cl:78][C:79]1[CH:84]=[CH:83][C:82]([Mg]Br)=[CH:81][CH:80]=1>C1COCC1>[CH2:40]([O:39][CH2:38][C:21]([CH2:58][O:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])([CH2:20][O:19][CH2:1][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])[CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([C:82]3[CH:83]=[CH:84][C:79]([Cl:78])=[CH:80][CH:81]=3)([OH:37])[C:26]=2[CH:25]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]

Participants

4

Reactant 2

HCID 594992402-(3-Octadecyloxy-2,2-bis-octadecyloxymethyl-propoxy)-9-fluorenoneHCID 178478191HCID 178478191, compound

Product 1

HCID 469277932-(3-Octadecyloxy-2,2-bis-octadecyloxymethyl-propoxy)-9-(4-chlorophenyl)-9-fluorenolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 2-(3-octadecyloxy-2,2-bis-octadecyloxymethyl-propoxy)-9-fluorenone (75 mg, 73 μmol) was suspended in THF (1 ml) to allow dissolution at 50° C. 4-Chlorophenylmagnesium bromide solution (0.15 ml, 0.15 mmol) was added dropwise, and the mixture was stirred for 30 minutes. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with chloroform (3 ml), and washed 3 times with 1N hydrochloric acid (1 ml), 3 times with 5% NaHCO3 solution (1 ml) and once with 20% NaCl solution (1 ml). The organic layer was dried over Na2SO4, the solvent of the filtrate was evaporated, and the obtained residue was separated and purified by silica gel column chromatography and crystallized from methanol (1 ml) to give 2-(3-octadecyloxy-2,2-bis-octadecyloxymethyl-propoxy)-9-(4-chlorophenyl)-9-fluorenol (66 mg, 56μ mmol, 77%).

Workup

  1. dissolutiondissolution at 50° C
  2. customAfter completion of the reaction
  3. extractionextracted with chloroform (3 ml)
  4. washwashed 3 times with 1N hydrochloric acid (1 ml), 3 times with 5% NaHCO3 solution (1 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent of the filtrate was evaporated
  7. customthe obtained residue was separated
  8. custompurified by silica gel column chromatography
  9. customcrystallized from methanol (1 ml)

Sources & evidence

ORD record
ord-589fbdd83a2344f489104a4ea31a551e
Source dataset
uspto-grants-2015_05
Patent number
US09029504B2

Reaction notes

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