2-Morpholinoethanol → HCID 15895515, compound

HRID 367039Notes

Reaction equation

HRID 367039 reaction equation
[OH:1][C:2]1([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[O:6][C:5](=[O:7])[C:4]([C:8]2[CH:16]=[C:15]([O:17][CH3:18])[C:11]3[O:12][CH2:13][O:14][C:10]=3[CH:9]=2)=[C:3]1[CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1.O[CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>ClCCl>[CH3:18][O:17][C:15]1[C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=[C:8]([C:4]2[C:5](=[O:7])[O:6][C:2]([C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)([O:1][CH2:41][CH2:42][N:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)[C:3]=2[CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 611632-MorpholinoethanolHCID 10530409HCID 10530409, compound

Product 1

HCID 15895515HCID 15895515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 125 mL dichloromethane was added 5-Hydroxy-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 3.25 g (6.06 mmol), giving a suspension. 4-(2-Hydroxyethyl)morpholine 3.24 g (24.76 mmol) was added, and the mixture was purged with anhydrous HCl gas until saturated. After 24 hours at room temperature, the mixture was evaporated in vacuo and the residue was suspended in warm ethyl ether and water. Decant the aqueous phase and wash the ether phase with 1 N NaOH, followed by water and saturated sodium chloride solution. The ether phase was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to a glassy solid, 2.13 g. The product was identified by 1H NMR, MS [M--H]+ =650 Da.

Workup

  1. customgiving a suspension
  2. customthe mixture was purged with anhydrous HCl gas until saturated
  3. customthe mixture was evaporated in vacuo
  4. customDecant the aqueous phase
  5. washwash the ether phase with 1 N NaOH
  6. dry with materialThe ether phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo to a glassy solid, 2.13 g

Sources & evidence

ORD record
ord-615fdb18e1f34273b4baeef5c333849b
Source dataset
uspto-grants-2000_10
Patent number
US06133263

Reaction notes

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