Phenyl isocyanate → 5-Isoxazolemethanol, 3-dodecyl-

HRID 865416Notes

Reaction equation

HRID 865416 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([O-:3])=O.C[Si](C)(C)[O:19][C:20]#[C:21][CH3:22].C1(N=C=O)C=CC=CC=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:5]([C:4]1[CH:22]=[C:21]([CH2:20][OH:19])[O:3][N:1]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 108233151-NitrotridecaneHCID 13614841O-trimethylsilylpropynol

Product 1

HCID 106355535-Isoxazolemethanol, 3-dodecyl-Yield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 1-nitrotridecane (10.5 g) and O-trimethylsilyl-propynol (5.88 g) in dry benzene (100 ml) was added dropwise a solution of freshly distilled phenylisocyanate (10.9 g) and triethylamine (5.56 g) in dry benzene (40 ml) at 40° C., with mechanical stirring. The mixture was heated to 60° C. for 3.5 hr, cooled, and filtered. The filtrate was evaporated, taken up in tetrahydrofuran (300 ml) and 1.0M tetrabutylammonium fluoride (8 ml) was added. After 30 mins, the mixture was evaporated and the residue was purified by flash chromatography (silica gel, 2% methanol:dichloromethane). The appropriate fractions were collected and evaporated to give 10.5 g (86%) of product, mp 61°-63° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. addition1.0M tetrabutylammonium fluoride (8 ml) was added
  5. customthe mixture was evaporated
  6. customthe residue was purified by flash chromatography (silica gel, 2% methanol:dichloromethane)
  7. customThe appropriate fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-54cfa0bb15eb469bafc6b5a505cb932c
Source dataset
uspto-grants-1996_10
Patent number
US05565584

Reaction notes

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