Potassium Carbonate → HCID 70277001, compound

HRID 1708442Notes

Reaction equation

HRID 1708442 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:14]2[CH2:18][CH2:17][C@H:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[O:15]2)[CH:6]=[C:7]([NH2:13])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH2:39][OH:40]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:14]2[CH2:18][CH2:17][C@H:16]([C:19]3[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=3)[O:15]2)[CH:6]=[C:7]([NH:13][CH2:38][CH2:39][OH:40])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 70277309HCID 70277309, compound

Product 1

HCID 70277001HCID 70277001, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of trans-2-(3-methoxy-4-propoxy-5-aminophenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (20 mg. 0.048 mmol), potassium carbonate (0.4 g), and 2-iodoethanol (82.47 mg, 0.48 mmol) was suspended in 2 mL of DMF. The reaction mixture was stirred at room temperature for 20 hours, quenched with water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo to an oil which was purified by column using 3:1 hexane/ethyl acetate as solvent (12.8 mg, 57.9%). 1H NMR (CDCl3): 1.02 (t, 3H), 1.79 (m, 2H), 1.99 (m, 2H), 2.43 (m, 2H), 3.33 (m, 2H), 3.81 (m, 2H), 3.82 (s, 3H), 3.83 (s, 3H), 3.88 (s, 6H), 3.90 (t, 2H), 5.18 (m, 2H), 6.40 (d, 2 H), 6.61 (s, 2H).

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo to an oil which
  6. customwas purified by column

Sources & evidence

ORD record
ord-498b6ff01e3d44de83cde2687b9159d8
Source dataset
uspto-grants-1994_10
Patent number
US05358938

Reaction notes

Loading…