Tetrahydrofuran → HCID 19018176, compound

HRID 1728454Notes

Reaction equation

C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:20])[C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)C.O1CCCC1.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:20])[C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:10]=1)=[O:3]

Participants

Conditions

Temperature: 20 °C

Procedure

To 185 g of 1-(4-diethoxymethylphenyl)-3-phenyl-prop-2-yn-1-ol in 1.8 liters of a 9:1 mixture of tetrahydrofuran and water were added 30 g of p-toluenesulfonic acid pyridinium salt. After stirring at 20° C. for 15 hours, 500 ml of a saturated aqueous solution of sodium bicarbonate were added. The organic layer was separated, and after drying over magnesium sulfate, the drying agent was separated, and ethyl acetate was distilled off at 40° C. and 2.7×103Pa to yield 131 g of 1-(4-formylphenyl)-3-phenylprop-2-yn-1-ol in the form of a yellow oil. The resulting oil was stirred together with 57.9 g of hydroxylamine hydrochloride and 44 g of sodium carbonate in 1.1 liters of tetrahydrofuran/water 4:1 at 20° C. for 15 hours. Then 500 ml of a saturated aqueous solution of sodium chloride were added. The reaction mixture was shaken with ethyl acetate. After drying the organic layer over magnesium sulfate, the drying agent was separated by filtration at 40° C. and 2.7×103Pa to yield 153 g of the oxime 1-(4-hydroxyiminomethylphenyl)-3-phenyl-prop-2-yn-1-ol, syn/anti-mixture, in the form of a colorless solid.

Workup

customThe organic layer was separated
dry with materialafter drying over magnesium sulfate
customthe drying agent was separated
distillationethyl acetate was distilled off at 40° C.

Sources & evidence

ORD record: ord-b012a61acf824c968114be4eb74f36ee
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326902

Reaction notes

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