Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)- → HCID 4983340, compound

HRID 2259992Notes

Reaction equation

HRID 2259992 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([CH3:18])=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[C:3]([CH:16]([OH:17])[CH3:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2×HCID 4311764Sodium borohydride

Product 1

HCID 4983340HCID 4983340, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.17 g (17.1 mmol) of methyl (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2yl) ketone (Compound 16) in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid.

Workup

  1. customat 0° C.
  2. customSolvent was removed in-vacuo
  3. extractionextracted three times with ether
  4. washThe ether extracts were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in-vacuo
  7. customresulting residue
  8. custompurified
  9. customto give a single isomer

Sources & evidence

ORD record
ord-fbff564a541d4c97831609263f33c595
Source dataset
uspto-grants-1995_12
Patent number
US05475113

Reaction notes

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