Dimethylformamide → HCID 86744130, compound

HRID 2166484Notes

Reaction equation

HRID 2166484 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][OH:11].[H-].[Na+].[H][H].CC([N:20]1[CH2:24][CH:23]([CH2:25][O:26]S(C2C(C)=CC=CC=2)(=O)=O)[O:22][CH:21]1[C:37]1[CH:42]=CC=C[CH:38]=1)(C)C.C(N1CC(CO)O[C@H]1[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)(C)(C)C.[CH3:60]N(C=O)C>O>[CH3:8][C:5]1[CH:6]=[C:7]([O:26][CH2:25][CH:23]2[O:22][CH:21]([C:37]([CH3:38])([CH3:42])[CH3:60])[NH:20][CH2:24]2)[C:2]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[C:3]([CH2:9][CH2:10][OH:11])[CH:4]=1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 12296652(S)-2-phenyl-3-tert-butyl-5-hydroxymethyloxazolidineHCID 15702966112395-77-4HCID 86744131HCID 86744131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86744130HCID 86744130, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 7.3 g (0.048 mol) of 2-(2-hydroxy-5-methylphenyl)ethanol in 30 ml of dry DMF was added 1.91 g (0.048 mol) of sodium hydride (60% in mineral oil). The mixture was stirred at room temperature until hydrogen evolution ceased, and the solution was heated at 60° C. for 30 minutes to insure complete reaction. The solution was cooled to room temperature, and to this solution was added 18.29 g of 3-(1,1-dimethylethyl)-2-phenyl-5-(toluenesulfonyloxymethyl)oxazolidine prepared by the reaction of 11.29 g (0.048 mol) of (S)-3-tert-butyl-5-hydroxymethyl-2-phenyloxazolidine with 9.15 g (0.048 mol) of p-tosylchloride. The solution was heated at 120° C. overnight. The cooled solution was poured onto 600 ml of water and this mixture was extracted with four 150 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed with water, dilute sodium hydroxide solution, water, and brine. The solution was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 16.1 g of crude product.

Workup

  1. customreaction
  2. temperatureThe solution was cooled to room temperature
  3. temperatureThe solution was heated at 120° C. overnight
  4. extractionthis mixture was extracted with four 150 ml portions of ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with water, dilute sodium hydroxide solution, water, and brine
  6. dry with materialThe solution was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0e2eb17c12a4f1597508ac87565ad26
Source dataset
uspto-grants-1990_07
Patent number
US04945182

Reaction notes

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