4-Chlorobenzyl alcohol → HCID 54305668, compound

HRID 1488945Notes

Reaction equation

HRID 1488945 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.Cl[C:13]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)=[CH:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16]>O1CCCC1.CN(C)C=O>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][C:13]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 53730792HCID 53730792, compound

Product 1

HCID 54305668HCID 54305668, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

0.3 g (10 mmol) of sodium hydride (80%) are stirred in 15 ml of tetrahydrofuran and 1.42 g (10 mmol) of 4-chlorobenzyl alcohol in 10 ml of tetrahydrofuran are added dropwise. The resulting clear solution is evaporated to dryness and a solution of 2.02 g (6.5 mmol) of 3-chloro-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one in 25 ml of dimethylformamide is added. The mixture is stirred at 90° C. for 20 hours. The solvent is then evaporated and the residue shaken with toluene/water. The organic phase is separated, washed with water, dried and purified over a flash column with 40 g of silicagel. Elution is carried out with toluene containing 10, 20 and 30% of acetone. The fractions with the TLC Rf-values 0.45 and 0.31 (toluene/acetone 7:3) are collected and evaporated.

Workup

  1. customThe resulting clear solution is evaporated to dryness
  2. customThe solvent is then evaporated
  3. stirringthe residue shaken with toluene/water
  4. customThe organic phase is separated
  5. washwashed with water
  6. customdried
  7. custompurified over a flash column with 40 g of silicagel
  8. washElution
  9. customThe fractions with the TLC Rf-values 0.45 and 0.31 (toluene/acetone 7:3) are collected
  10. customevaporated

Sources & evidence

ORD record
ord-e1463cda10a34129b429fa2219051f09
Source dataset
uspto-grants-1997_10
Patent number
US05677303

Reaction notes

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