Ethanol → HCID 19848772, compound

HRID 1153897Notes

Reaction equation

O[CH:2]1[O:26][C:10]2=[CH:11][C:12]([O:14][CH:15]([CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:16])=[CH:13][C:8]3=[C:9]2[CH:4]([CH2:5][C:6]([CH3:28])([CH3:27])[O:7]3)[CH2:3]1.C(O)C.[CH3:32][O:33][NH2:34]>N1C=CC=CC=1>[CH3:32][O:33][NH:34][CH:2]1[O:26][C:10]2=[CH:11][C:12]([O:14][CH:15]([CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:16])=[CH:13][C:8]3=[C:9]2[CH:4]([CH2:5][C:6]([CH3:27])([CH3:28])[O:7]3)[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

In a stirred flask, under nitrogen, was placed (0.045 mole) 2-hydroxy-5,5-dimethyl-8-(5-phenyl-2-pentyloxy)-3,3a,4,5-tetrahydro-2H-pyrano[4,3,2-de]benzopyran, 250 ml ethanol and 250 ml pyridine. The solution was cooled to 0° C. and 3.94 g (0.047 mole) methoxyamine was added. The resulting mixture was stirred at 0° C. for 2.5 hours, the solvent evaporated in vacuo, the residue taken up in 500 ml ethyl ether and washed twice with water. The aqueous phase was backwashed with ether and the combined ether layers washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to obtain 19 g of residual oil. The structure of the product was verified by 1H-NMR. Mass spectrum (m/e): 411 (M+), 380 (M-OCH3), 364 (M-NH2OCH3).

Workup

customIn a stirred flask, under nitrogen, was placed
customthe solvent evaporated in vacuo
washwashed twice with water
washthe combined ether layers washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-56abc582be1b43728cd5f907ffeb7030
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04486428

Reaction notes

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