Ethanol → HCID 20193536, compound

HRID 2118905Notes

Reaction equation

HRID 2118905 reaction equation
[OH:1][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.[CH2:29](O)C.CON>N1C=CC=CC=1>[CH3:29][O:1][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:21]=[CH:22][CH:23]=[CH:24][CH:25]=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

5

Reactant 3

HCID 702EthanolHCID 4113O-MethylhydroxylamineHCID 19848817HCID 19848817, compound

Product 1

HCID 20193536HCID 20193536, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 anydrous 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

  1. customIn a stirred flask, under nitrogen, was placed
  2. customthe solvent evaporated in vacuo
  3. washwashed twice with water
  4. washthe combined ether layers washed with brine
  5. dry with materialdried over anydrous magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-91853862737b470d8b13801748ab5c0a
Source dataset
uspto-grants-1987_07
Patent number
US04680404

Reaction notes

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