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Sodium borohydride → Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methanol

HRID 2104492
Notes
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Reaction equation

HRID 2104492 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CCO>[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:26])[F:27])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11360909Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone

Product 1

HCID 11222693Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]MethanolYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (Example 1, 0.200 g, 0.53 mmol) was taken into EtOH (5 mL) and cooled to 0° C. where was added NaBH4 (0.020 g, 0.53 mmol). The ice bath was removed and the reaction was allowed to stir at room temperature overnight. The EtOH was removed and water was added to the resulting material, where it was extracted with methylene chloride, dried over sodium sulfate and concentrated. The product was purified via column chromatography using 15% ethyl acetate in hexane as the eluent to afford 0.194 g of desired product as a white solid. MS (ESI) m/z 380 ([M+H]+); Anal. Calcd for C23H16F3NO: C, 72.82; H, 4.25; N, 3.69. Found: C, 72.52; H, 4.20; N, 3.55.

Workup

  1. customThe ice bath was removed
  2. customThe EtOH was removed
  3. additionwater was added to the resulting material, where it
  4. extractionwas extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified via column chromatography

Sources & evidence

ORD record
ord-18116b48dff241ee91639aa6ce758f13
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576215B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes