2,2,3,3-Tetrafluoro-1-propanol → HCID 86690530, compound

HRID 2172363Notes

Reaction equation

HRID 2172363 reaction equation
[CH2:1]([CH:3]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:4][N:5]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:14]([CH:22]=[O:23])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1F)[CH:10]=2)[CH3:2].[F:37][C:38]([F:44])([CH:41]([F:43])[F:42])[CH2:39][OH:40].[OH-].[Na+]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:4][N:5]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:14]([CH:22]=[O:23])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:40][CH2:39][C:38]([F:44])([F:37])[CH:41]([F:43])[F:42])[CH:10]=2)[CH3:2]

Participants

5

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 14798Sodium HydroxideHCID 86690528HCID 86690528, compound

Product 1

HCID 86690530HCID 86690530, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To 11-(2-ethylhexyl)-8-(2-fluorobenzoyl)-11H-benzo[a]carbazole-5-carbaldehyde (1.73 g, 3.60 mmol) in pyridine (18 ml) are added 2,2,3,3-tetrafluoropropanol (0.72 g, 5.48 mmol) and sodium hydroxide (0.24 g, 6.00 mmol) at room temperature. The reaction mixture is heated at 70° C. After stirring for 3 hours, the reaction mixture is poured into ice-water. The crude product is extracted with CH2Cl2 and washed with water and brine. After drying over MgSO4 and concentration, the product is reprecipitated from hexane and ethylacetate to obtain an off-white solid (1.91 g, 89%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.83-0.89 (m), 1.19-1.51 (m), 2.26 (m), 4.32 (t), 4.72 (m), 5.29 (t), 7.03 (d), 7.26 (t), 7.56-7.61 (m), 7.69-7.78 (m), 8.07 (d), 8.58 (d), 8.60 (s), 8.61 (s), 10.39 (s); 19F-NMR spectrum (CDCl3). δ [ppm] −140.92, −126.30.

Workup

  1. extractionThe crude product is extracted with CH2Cl2
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4 and concentration
  4. customthe product is reprecipitated from hexane and ethylacetate

Sources & evidence

ORD record
ord-8b2eff1ed97e4d849350ff726a6d2037
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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