Phenyl isocyanate → 3-(1-Decyl)-5-isoxazolemethanol

HRID 2301458Notes

Reaction equation

HRID 2301458 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([O-:3])=O.C[Si](C)(C)[O:17][C:18]#[C:19][CH3:20].C1(N=C=O)C=CC=CC=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:5]([C:4]1[CH:20]=[C:19]([CH2:18][OH:17])[O:3][N:1]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 109873051-NitroundecaneHCID 13614841O-trimethylsilylpropynol

Product 1

HCID 183729453-(1-Decyl)-5-isoxazolemethanolYield 34.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 1-nitroundecane (38.0 g) and O-trimethylsilylpropynol (24.1 g) in dry benzene (300 ml) was added dropwise a solution of freshly distilled phenylisocyanate (44.9 g) and triethylamine (22.4 g) in dry benzene (50 ml) at 40° C., with stirring. The reaction mixture was heated at 60° C. for 3 hrs, cooled, and filtered. To the filtrate was added 1.0 M tetrabutylammonium fluoride (40 ml). After 30 mins, the solution was evaporated, and the residue was flash chromatographed (silica gel, 1% methanol-dichloromethane) to give 15.5 g (34%) of product, mp 55-56° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. additionTo the filtrate was added 1.0 M tetrabutylammonium fluoride (40 ml)
  4. customthe solution was evaporated
  5. customchromatographed (silica gel, 1% methanol-dichloromethane)

Sources & evidence

ORD record
ord-d889d112dc7144a78f9b41da6deaf5b9
Source dataset
uspto-grants-2002_12
Patent number
US06500849B1

Reaction notes

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