Triethylamine → 4-Isocyanato-4-methyloxane

HRID 1798924Notes

Reaction equation

HRID 1798924 reaction equation
C[C:2]1([C:8](O)=O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C([N:13]([CH2:16]C)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:19].[OH-].[Na+]>C1(C)C=CC=CC=1>[N:13]([C:2]1([CH3:8])[CH2:3][CH2:4][O:5][CH2:6][CH2:7]1)=[C:16]=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 123414Diphenylphosphoryl azideHCID 115718204-METHYLTETRAHYDRO-2H-PYRAN-4-CARBOXYLIC ACID

Product 1

HCID 722137684-Isocyanato-4-methyloxaneYield 42.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A stirred solution of 4-methyltetrahydro-2H-pyran-4-carboxylic acid (D9) (1.26 g, 8.74 mmol) in Toluene (50 mL) at room temperature under argon was treated with triethylamine (1.58 mL, 11.36 mmol) and diphenyl azidophosphate (1.88 mL, 8.74 mmol) and heated to 85° C. for 2 hr. The mixture was allowed to cool to room temperature, then treated with 1 M NaOH solution (40 mL) and extracted with Et2O (3×). The combined extract was dried (Na2SO4), filtered and concentrated under vacuum to give the title compound (D10) (520 mg, 34%) as a yellow oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with Et2O (3×)
  3. extractionThe combined extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8e1e05a3adb44435b5551640396cee20
Source dataset
uspto-grants-2013_01
Patent number
US08344000B2

Reaction notes

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