Sodium borohydride → 1,1,1,3,3,3-Hexafluoro-2-(4-(hydroxymethyl)-3-propylphenyl)propan-2-ol

HRID 1807804Notes

Reaction equation

HRID 1807804 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([CH2:17][CH2:18][CH3:19])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[BH4-].[Na+]>CO.ClCCl>[F:1][C:2]([F:20])([F:21])[C:3]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[C:11]([CH2:17][CH2:18][CH3:19])[CH:10]=1)([OH:8])[C:4]([F:5])([F:7])[F:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866385824-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylbenzaldehyde

Product 1

HCID 866385831,1,1,3,3,3-Hexafluoro-2-(4-(hydroxymethyl)-3-propylphenyl)propan-2-olYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylbenzaldehyde (0.636 mmol, 200 mg) was dissolved in methanol (4 mL)/dichloromethane (1 mL) and sodium borohydride (1.909 mmol, 72.2 mg) was added. The mixture was stirred at room temperature for 90 minutes then was concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 mL) and washed with a saturated solution of sodium bicarbonate (25 mL). The organic phase was filtered through a hydrophobic frit and concentrated to afford the title compound (161 mg). MS (ESI) m/z 315.1 [M−H]

Workup

  1. additionwas added
  2. concentrationthen was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. washwashed with a saturated solution of sodium bicarbonate (25 mL)
  5. filtrationThe organic phase was filtered through a hydrophobic frit
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82fe0671b3e74bd380430390707bbb50
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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