Methanol → 5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanecarbonitrile

HRID 16229Notes

Reaction equation

HRID 16229 reaction equation
CC(C)([O-])C.[K+].S([CH2:17][N+:18]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CO.[C:22]([Si:26]([CH3:38])([CH3:37])[O:27][CH:28]1[CH2:35][CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30][CH2:29]1)([CH3:25])([CH3:24])[CH3:23]>COCCOC>[C:22]([Si:26]([CH3:38])([CH3:37])[O:27][CH:28]1[CH2:35][CH2:34][CH2:33][CH:32]([C:17]#[N:18])[CH2:31][CH2:30][CH2:29]1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 161915Tosylmethyl isocyanideHCID 109780905-(Tert-butyldimethylsilyloxy)cyclooctanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 666569295-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanecarbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Potassium tert-butoxide (30.4 mL, 1 M in tetrahydrofuran, 30.4 mmol) was added drop wise to a stirred and cooled (0° C.) solution of tosylmethyl isocyanide (4.74 g, 24.27 mmol) in dry DME (40 mL). After ten minutes, dry methanol (0.98 mL, 24.28 mmol) was added and followed by a solution of the product of Example 5B (3.11 g, 12.14 mmol) in DME (10 mL). The resulting solution was allowed to warm to room temperature and then heated (45° C.) for thirty minutes. After cooling, the reaction mixture was partitioned with diethyl ether and water. The organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 2-10% diethyl ether in hexanes to give the title compound as an oil.

Workup

  1. waitAfter ten minutes
  2. temperatureheated (45° C.) for thirty minutes
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned with diethyl ether and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified over silica gel using 2-10% diethyl ether in hexanes

Sources & evidence

ORD record
ord-50778fe737ce4361906f6b8f685034de
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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