Sodium borohydride → HCID 178490601, compound

HRID 604669Notes

Reaction equation

HRID 604669 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109765814-(4-Methoxyphenyl)cyclohexanone

Product 1

HCID 178490601HCID 178490601, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Methoxyphenyl)cyclohexanone (400 mg, 1.958 mmol) was dissolved in MeOH (20 mL) and cooled to 0° C. NaBH4 (222 mg, 5.87 mmol) was added, and the reaction was stirred at 0° C. for 30 min. The reaction was then quenched with 5 mL of water, stirred for 5 min, and then diluted with EtOAc (50 mL). The organic layer was washed with water (3×50 mL) and brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 70% EtOAc/hexanes) to afford trans-4-(4-methoxyphenyl)cyclohexanol. 1H NMR (500 MHz, CDCl3): δ 7.12 (d, J=8.5 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 3.79 (s, 3H), 3.68 (m, 1H), 2.46 (m, 1H), 2.07-2.12 (m, 2H), 1.86-1.94 (m, 3H), 1.38-1.54 (m, 4H).

Workup

  1. customThe reaction was then quenched with 5 mL of water
  2. stirringstirred for 5 min
  3. additiondiluted with EtOAc (50 mL)
  4. washThe organic layer was washed with water (3×50 mL) and brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (0 to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7c37abf44cf84573895175624334e1d0
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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