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

HRID 1722026Notes

Reaction equation

HRID 1722026 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 (3X). 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 (3X)
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e6ffced05b2046e69b4f02e0ca263b05
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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