Benzaldehyde → [2-Phenyl-3-(4-phenylbutan-2-yl)-1,3-oxazolidin-5-yl]methanol

HRID 235977Notes

Reaction equation

HRID 235977 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([NH:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:18]1([CH:17]2[N:11]([CH:9]([CH3:10])[CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH:13]([CH2:14][OH:15])[O:16]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 51955603-(1-Phenyl-3-butyl)amino-1,2-propanediol

Product 1

HCID 53876813[2-Phenyl-3-(4-phenylbutan-2-yl)-1,3-oxazolidin-5-yl]methanolYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 94 (24 g, 0.108 mol), toluene, benzaldehyde (40 ml) and benzoic acid (0.5 g) was heated at reflux with a Dean-Stark trap. After 1 hour, the theoretical amount of H2O was collected, the reaction cooled to room temperature and saturated Na2CO3 added. The aqueous layer was separated and washed with CHCl3 (3×). The combined extracts were dried, filtered and concentrated to dryness to yield 34 g (100%) of 95.

Workup

  1. temperatureat reflux with a Dean-Stark trap
  2. customthe theoretical amount of H2O was collected
  3. additionsaturated Na2CO3 added
  4. customThe aqueous layer was separated
  5. washwashed with CHCl3 (3×)
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6b97cba6a0d745b1b69434365d1d9a68
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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