Tyrosol → HCID 54082836, compound

HRID 978466Notes

Reaction equation

HRID 978466 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H-].[Na+].[C:13]1([C@H:19]2[N:23]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:22][CH:21]([CH2:28]OS(C3C=CC(C)=CC=3)(=O)=O)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH3:25][C:24]([N:23]1[CH2:22][CH:21]([CH2:28][O:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=2)[O:20][C@H:19]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 10393TyrosolHCID 24758Sodium hydrideHCID 53982628HCID 53982628, compound

Product 1

HCID 54082836HCID 54082836, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-(2-Hydroxyethyl)phenol (2.5 g, 18 mmol) was dissolved in 37 ml DMF then NaH (60% in mineral oil) (0.72 g, 18 mmol) was added while stirring under N2 atmosphere. After the evolution of H2 ceased, (S)-2-phenyl-5-tosyloxymethyl-3-(1,1-dimethylethyl) oxazolidine (7.0 g, 18 mmol) in 25 ml DMF was added and the reaction mixture was heated at 115°-120° C. for 14 hours. The solvent was evaporated in vacuo. A sodium carbonate solution (100 ml, 20% saturated) was added to the residue and the mixture was extracted with CHCl3 (150 ml then 100 ml). The chloroform was removed in vacuo and the residue was used directly in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated at 115°-120° C. for 14 hours
  2. customThe solvent was evaporated in vacuo
  3. additionA sodium carbonate solution (100 ml, 20% saturated) was added to the residue
  4. extractionthe mixture was extracted with CHCl3 (150 ml
  5. customThe chloroform was removed in vacuo
  6. customthe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-1f0eace6a1cc43579f4b77c3041fd19d
Source dataset
uspto-grants-1987_05
Patent number
US04665094

Reaction notes

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