Triethylamine → HCID 22126317, compound

HRID 1005193Notes

Reaction equation

HRID 1005193 reaction equation
ClN1C(=O)CCC1=O.[CH:9](=[N:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH2:25]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[C:26]#[CH:27]>C(Cl)Cl>[C:10]1([C:9]2[CH:27]=[C:26]([CH2:25][O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[O:17][N:16]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398ChlorosuccinimideHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyran

Product 1

HCID 22126317HCID 22126317, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.47 g (11 mmol) of N-chlorosuccinimide were added at -30° C. to a solution of 1.21 g of benzaldoxime in 10 ml of methylene chloride. After 2 hours a solution of 1.0 g of triethylamine and 1.4 g of (RS)-tetrahydro-2-(2-propynyloxy)-2H-pyran in 5 ml of methylene chloride was added dropwise. The reaction mixture was stirred at room temperature for 5 hours, the solvent was thereafter distilled off and, for purification, the crude product was chromatographed on silica gel using methylene chloride as the eluent. There were obtained 1.8 g of (RS)-3-phenyl-5-(tetrahydro-pyran-2-yloxymethyl)-isoxazole as a colourless liquid; MS: 259 (M)+.

Workup

  1. distillationthe solvent was thereafter distilled off and, for purification
  2. customthe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-797973daa27c4a10afe74961c20329ba
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

Loading…