Triethylamine → HCID 18381626, compound

HRID 2268839Notes

Reaction equation

HRID 2268839 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[CH:15]([OH:26])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3]1.C(N(CC)CC)C.S(=O)(=O)=O.[NH+]1C=CC=CC=1>CS(C)=O.O>[CH3:1][C:2]1([CH3:27])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18381637HCID 18381637, compoundHCID 23037722HCID 23037722, compound

Product 1

HCID 18381626HCID 18381626, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-5-phenyl-pentan-1-ol (0.62 g, 1.7 mmoles), prepared as described in example 17, in DMSO (10 ml) was added with triethylamine (35 ml) and, after 30 minutes, with pyridinium sulfur trioxide (1.62 g, 10.2 mmoles). After 6 hours, the mixture was diluted with 10 volumes of water and twice extracted with ethyl ether. The organic phases were washed with water, discoloured with charcoal, anhydrified and concentrated. The residue was flash chromatographed (eluent: petrolatum/ethyl acetate 7:3) to give 0.37 g of the title compound (yield: 60%).

Workup

  1. extractiontwice extracted with ethyl ether
  2. washThe organic phases were washed with water
  3. concentrationconcentrated
  4. customchromatographed (eluent: petrolatum/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-0e331ee041cf4a4a94c8d4b963fdc48a
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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