Tosylmethyl isocyanide → HCID 19390026, compound

HRID 1757227Notes

Reaction equation

HRID 1757227 reaction equation
CC([O-])(C)C.[K+].S([CH2:17][N+:18]#[C-])(C1C=CC(C)=CC=1)(=O)=O.O[CH:21]1[CH2:26][CH2:25][C:24]2([CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]2)[CH2:23][CH2:22]1>O1CCCC1.C(O)C>[OH:32][CH:29]1[CH2:30][CH2:31][C:24]2([CH2:25][CH2:26][CH:21]([C:17]#[N:18])[CH2:22][CH2:23]2)[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 19390049HCID 19390049, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19390026HCID 19390026, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butylate (1.44 g) was added in small portions, at 0° C. under nitrogen atmosphere, to a solution of 1.40 g of tosylmethylisocyanide and 1.00 g of 3-hydroxy-9-oxo-spiro[5.5]undecane (II-a, Prep. 1) dissolved in 7 ml of anhydrous tetrahydrofuran and 0.53 ml of absolute ethanol. After 0.5 hrs at room temperature, the mixture was filtered on an alumina cake. The cake was washed with dichloromethane and the filtrates, dried over anhydrous sodium sulfate, were evaporated under reduced pressure to give 0.52 g of crude 9-hydroxy-3-cyano-spiro[5.5]undecane as a light oil. [TLC: Rf=0.52 (SiO2 plates, diethylether). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 3.63 (1H, hept), 2.57 (1H, m), 1.90-1.05 (16H, m)].

Workup

  1. filtrationthe mixture was filtered on an alumina cake
  2. washThe cake was washed with dichloromethane
  3. dry with materialthe filtrates, dried over anhydrous sodium sulfate
  4. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-a4a230e91d8649fb831db75935672cea
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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