Quinone → 3-Methyl-2-(morpholin-4-yl)-2,3-dihydro-1-benzofuran-5-ol

HRID 1504257Notes

Reaction equation

HRID 1504257 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:10][CH3:11]>C1(C)C=CC=CC=1>[CH3:11][CH:10]1[C:3]2[CH:2]=[C:1]([OH:8])[CH:6]=[CH:5][C:4]=2[O:7][CH:9]1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 4650QuinoneHCID 544254874-(Prop-1-en-1-yl)morpholine

Product 1

HCID 138729953-Methyl-2-(morpholin-4-yl)-2,3-dihydro-1-benzofuran-5-olYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzoquinone (300 g, 2.8 mol) was added in toluene (1.5 L) and cooled with a dry ice/isopropyl alcohol (IPA) bath. 4-Propenyl-morpholine (prepared as above in EXAMPLE I) (380 g, 3 mol) was added dropwise with stirring. The reaction mixture was aged for overnight, filtered and subsequently air dried to provide 3-methyl-2-morpholin-4-yl-2,3-dihydro-benzofuran-5-ol (628 g, 2.7 mol).

Workup

  1. temperaturecooled with a dry ice/isopropyl alcohol (IPA) bath
  2. filtrationfiltered
  3. customsubsequently air dried

Sources & evidence

ORD record
ord-909b60085f2b42fe993991ecbf59c4df
Source dataset
uspto-grants-2015_12
Patent number
US09212336B2

Reaction notes

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