Ethanol → HCID 15112858, compound

HRID 409376Notes

Reaction equation

HRID 409376 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][C:5]=1[CH:6]=[O:7])([CH3:3])[CH3:2].CCO.[BH4-].[Na+].CCCCCCC>CCOC(C)=O>[CH:1]([C:4]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][C:5]=1[CH2:6][OH:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8900HeptaneHCID 4311764Sodium borohydrideHCID 125701012,5-Bis(1-methylethyl)benzaldehyde

Product 1

HCID 15112858HCID 15112858, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 2-neck RBF equipped with magnetic stir bar and N2 inlet, 2,5-diisopropylbenzaldehyde (1.7 g, 9 mmol) was dissolved into 30 mL of EtOH and NaBH4 (0.37 g, 10 mmol) was added over 20 min (portion-wise). After 18 h stirring at RT, ˜95% of solvent was removed on a rotary evaporator and then 5 mL of 0.5 M HCl was added and product was extracted with 25 mL of EtOAc. Organic layer was washed with 15 mL of H2O and 15 mL of brine, dried over Na2SO4, filtered and concentrated to dryness to obtain crude product. This material was subjected to chromatography using heptane: EtOAc as mobile phase to provide 1.1 g of pure product. Yield 65%. 1H NMR (300 MHz, CDCl3) δ 1.2-1.3 (d, 12H), 2.8 (septet, 1H), 3.2 (septet, 1H), 5.7 (s, 2H), 7.1-7.3 (m, 3H).

Workup

  1. customIn a 2-neck RBF equipped with magnetic stir bar and N2 inlet
  2. additionwas added over 20 min (portion-wise)
  3. custom˜95% of solvent was removed on a rotary evaporator
  4. addition5 mL of 0.5 M HCl was added
  5. extractionproduct was extracted with 25 mL of EtOAc
  6. washOrganic layer was washed with 15 mL of H2O and 15 mL of brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customto obtain crude product

Sources & evidence

ORD record
ord-a8163e3ea27947828deb763e29fa9292
Source dataset
uspto-grants-2014_06
Patent number
US08759340B2

Reaction notes

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