Sodium Hydroxide → HCID 18783157, compound

HRID 1420872Notes

Reaction equation

HRID 1420872 reaction equation
[CH3:1][C:2]1(O)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.C[Si]([C:17]#[N:18])(C)C.[OH-:19].[Na+]>C(O)(=O)C>[CH:17]([NH:18][C:2]1([CH3:1])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:11])([CH3:10])[CH2:3]1)=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 1422881,3,3,5,5-Pentamethylcyclohexanol

Product 1

HCID 18783157HCID 18783157, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a vigorously stirred solution of 1,3,3,5,5-pentamethylcyclohexanol (3-13) (2.7 g, 15.6 mmol) and trimethylsilyl cyanide (2.36 g, 23.8 mmol) in acetic acid (2.5 ml) under argon 98% sulfuric acid (4.66 g, 47.6 mmol) was added, keeping temperature below -5° C. The mixture was stirred at room temperature for 22 h, then it was poured onto ice (100 g), neutralised with 50% NaOH solution to pH ~7 and extracted with ether (3*30 ml). The combined ether phases were washed with saline (50 ml), then dried over MgSO4 and evaporated. A slightly yellow crystalline residue was treated with small amount of acetonitrile and filtered off to give 2.5 g (80%) of 14-1 as a white crystals, m.p. 104-106° C. 1H NMR (CDCl3, TMS) δ: 0.91 and 0.93 (total 6H, both s, 3,5-CH3eq); 1.08 (2H, m, 2,6-CHeq); 1.13 and 1.15 (total 6H, both s, 3,5-CH3ax); 1.25 (2H, m, 4-CH2); 1.32 and 1.38 (total 3H, both s, 1-CH3); 1.70 and 2.12 (total 2H, both d, 14.7 Hz, 2,6-CHax); 5.30 and 5.60 (total 1H, both br s, NH); 8.05 and 8.30 ppm (total 1H, both d, 2.0 and 12.7 Hz, resp., HCO).

Workup

  1. customtemperature below -5° C
  2. additionit was poured onto ice (100 g)
  3. extractionextracted with ether (3*30 ml)
  4. washThe combined ether phases were washed with saline (50 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additionA slightly yellow crystalline residue was treated with small amount of acetonitrile
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-7dba61c9a1dc47cebe09522e00a9967b
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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