1,4-Dioxaspiro[4.5]decan-8-one → 1,4-Dioxaspiro[4.5]decane-8-carbonitrile

HRID 844009Notes

Reaction equation

HRID 844009 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.S([CH2:22][N:23]=C=O)(C1C=CC(C)=CC=1)(=O)=O.C(O[K])(C)(C)C>CN(C)C=O.O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:22]#[N:23])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzeneHCID 178418922HCID 178418922, compound

Product 1

HCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrileYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,4-Dioxa-spiro[4,5]decan-8-one (2.0 grams, 12.8 mmole) and tosyl-methyl isocyanate (5.0 grams, 25.6 mmole) in dimethylformamide (25 ml) at 0° C. was added 1.0 M tBuOK in tButanol (25.6 ml) and stirred at 0° C. for 1 hour and room temperature over night. The mixture was diluted with water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to a solid which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent to give a solid (1.45 g). MW 167.209; MS (m/e) 168 (M++1).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a solid which
  6. customwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-a31e2c674bd446dfa7f8fb587360f5fd
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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