Sodium Hydroxide → HCID 89627666, compound

HRID 2203246Notes

Reaction equation

HRID 2203246 reaction equation
[CH2:1]([CH:3]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=3)=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:31](=[O:40])[CH2:32][CH:33]([CH3:39])[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:10]=2)[CH3:2].[F:45][C:46]([F:60])([C:49]([F:59])([F:58])[C:50]([F:57])([F:56])[C:51]([F:55])([F:54])[CH2:52][OH:53])[CH2:47][OH:48].[OH-:61].[Na+]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([O:53][CH2:52][C:51]([F:54])([F:55])[C:50]([F:57])([F:56])[C:49]([F:58])([F:59])[C:46]([F:60])([F:45])[CH2:47][O:48][C:26]4[CH:27]=[CH:28][C:23]([C:22]([C:14]5[C:15]6[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=6[C:17]6[N:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:41][CH2:42][CH2:43][CH3:44])[C:6]7[C:11]([C:12]=6[CH:13]=5)=[CH:10][C:9]([C:31](=[O:40])[CH2:32][CH:33]([CH3:39])[CH2:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:8][CH:7]=7)=[O:61])=[CH:24][CH:25]=4)=[CH:25][CH:24]=3)=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:31](=[O:40])[CH2:32][CH:33]([CH3:39])[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:10]=2)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1361812,2,3,3,4,4,5,5-Octafluorohexane-1,6-diolHCID 117689280HCID 117689280, compound

Product 1

HCID 89627666HCID 89627666, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To 1-[11-(2-ethylhexyl)-5-(4-fluoro-benzoyl)-11H-benzo[a]carbazol-8-yl]-3,5,5-trimethyl-hexan-1-one (1.18 g; 2.00 mmol) in pyridine (5 mL) are added 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (0.24 g; 0.90 mmol) and sodium hydroxide (0.16 g; 4 mmol) at 80° C., and the mixture is stirred at 100° C. for 43 hours. After the reaction is completed, the reaction mixture is cooled to room temperature, and poured into ice water. The crude product is extracted with ethyl acetate, and the combined organic layer is washed with water and brine, dried over MgSO4, and concentrated to give a yellow resin. The crude is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1) to give a yellow solid (0.40 g; 32%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.81-0.92 (m), 1.03 (d), 1.18-1.46 (m), 2.27-2.35 (m), 2.89-2.96 (m), 3.02-3.08 (m), 4.60 (t), 4.74 (m), 7.06 (d), 7.58 (m), 7.66 (t), 7.99 (m), 8.14 (dd), 8.33 (s), 8.43 (d), 8.61 (d), 8.68 (d); 19F-NMR spectrum (CDCl3). δ [ppm]: −123.32, −119.45.

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. extractionThe crude product is extracted with ethyl acetate
  3. washthe combined organic layer is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow resin
  7. customThe crude is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1)
  8. customto give a yellow solid (0.40 g; 32%)

Sources & evidence

ORD record
ord-9c9a268440ec4547b227365706b31300
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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