Sodium borohydride → HCID 12251285, compound

HRID 2398811Notes

Reaction equation

HRID 2398811 reaction equation
CO[C:3]1[CH2:4][C:5]2([CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[BH4-].[Na+]>C(O)C>[C:5]12([CH2:13][CH2:14][CH:15]([OH:18])[CH2:16][CH2:17]1)[C:6]1[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:12][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21433605HCID 21433605, compound

Product 1

HCID 12251285HCID 12251285, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a partial solution of 5.10 g. (0.038 M) of 3',4'-dihydrospiro[cyclohexane-1,1'(2'H)-naphthalen]-4-one(r) (prepared as in Example 16A) in 105 ml. of 95% ethanol, 2.59 g. of sodium borohydride is added and the mixture stirred at room temperature for about 4 hours. Most of the solvent is removed under vacuum and water added to the residue. The material that precipitates is extracted with ether and the combined extracts washed with water and brine and evaporated to dryness. The residue is recrystallized once from Skellysolve B and then chromatographed over a column containing 500 ml. of silica gel with elution by 10% acetone:Skellysolve B. On the basis of TLC the less polar fractions are combined and recrystallized from benzene:cyclohexane to give a small amount of 3',4'-dihydrospiro[cyclohexane-1,1'(2'H)-naphthalen]-4-ol(s), having a melting point of 144.5° to 146° C., and an NMR spectrum suggesting that the compound has the hydroxy substituent in the axial position.

Workup

  1. customMost of the solvent is removed under vacuum and water
  2. additionadded to the residue
  3. customThe material that precipitates
  4. extractionis extracted with ether
  5. washthe combined extracts washed with water and brine
  6. customevaporated to dryness
  7. customThe residue is recrystallized once from Skellysolve B
  8. customchromatographed over a column
  9. additioncontaining 500 ml
  10. washof silica gel with elution by 10% acetone
  11. customrecrystallized from benzene

Sources & evidence

ORD record
ord-4c4a36ede15f41279cbf07669aa1a410
Source dataset
uspto-grants-1977_05
Patent number
US04025558

Reaction notes

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