Diethyl Ether → 3-(3'-Ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol

HRID 1941242Notes

Reaction equation

HRID 1941242 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH2:15][CH3:16])[CH:7]=1)[CH2:3][CH2:4][OH:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(OCC)=O.CCOCC>C(#N)C.O.CCCCCC>[CH2:15]([O:14][C:8]1[CH:7]=[C:6]([CH:2]([N:1]2[C:32](=[O:33])[C:31]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]3[C:29]2=[O:38])[CH2:3][CH2:4][OH:5])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13])[CH3:16]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 221771793-Amino-3-(3-ethoxy-4-methoxyphenyl)propan-1-ol

Product 1

HCID 214605203-(3'-Ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

A mixture of 3-amino-3-(3'-ethoxy-4'-methoxyphenyl)-1-propanol (8.4 grams, 37.3 mmol) and sodium carbonate (3.95 grams, 37.3 mmol) in acetonitrile and water (40 mL each) was stirred at room temperature for 15 minutes. To the solution was added N-carbethoxyphthalimide (8.18 grams, 37.3 mmol) as solid. After 20 minutes, the acetonitrile was removed under vacuum. The aqueous solution was extracted with methylene chloride (3×50 mL). The combined organic layers were washed with HCl (40 mL, 1N), and dried over magnesium sulfate. Removal of solvent gave a green oil. Ether (25 mL) was added to the oil, then hexane (2 mL) was added. A suspension formed and the solid was filtered to give 3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol as a white solid, 1 g. The mother liquor was purified by chromatography (silica gel 500 grams, 10, 15, 20% EtOAc/CH2Cl2) to give 3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol as a solid, 2.54 g. Total yield was 3.54 g (27% yield): mp, 112.0°-114.0° C.; 1H NMR (CDCl3)δ1.45 (t, J=7 Hz, 3H, CH3), 1.59-1.65 (br s, 1H, OH), 2.49-2.59 (m, 1H, CHH), 2.71-2.83 (m, 1H, CHH), 3.66-3.69 (m, 2H, OCH2), 3.84 (s, 3H, CH3), 4.10 (q, J=7 Hz, 2H, MeCH2), 5.53 (dd, J=6.5, 9.5 Hz, 1H, NCH), 6.81 (d, J=8.2 Hz, 1H, Ar), 7.09-7.27 (m, 2H, Ar), 7.66-7.72 (m, 2H, Ar), 7.76-7.82 (m, 2H, Ar); 13C NMR (CDCl3)δ14.72, 33.86, 51.46, 55.88, 59.84, 64.34, 111.16, 113.05, 120.68, 123.20, 131.64, 131.86, 133.94, 148.17, 148.97, 168.49; Anal Calcd for C20H21NO5 : C, 67.59; H, 5.96; N, 3.94. Found: C, 65.40; H, 5.81; N, 3.84.

Workup

  1. waitAfter 20 minutes
  2. customthe acetonitrile was removed under vacuum
  3. extractionThe aqueous solution was extracted with methylene chloride (3×50 mL)
  4. washThe combined organic layers were washed with HCl (40 mL, 1N)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent
  7. customgave a green oil
  8. customA suspension formed
  9. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-d0601533ac6d41ec976770f7126cb598
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

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