Oxolane--water (1/1) → 4-(4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

HRID 1692094Notes

Reaction equation

HRID 1692094 reaction equation
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[CH:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:40]CC1.O>O=[Os](=O)(=O)=O>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[CH:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=[O:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21881883Oxolane--water (1/1)HCID 666219154-Benzyl-3-[2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one

Product 1

HCID 723121104-(4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehydeYield 28.5%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Dissolve 4-Benzyl-3-[2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (3.09 g, 5.89 mmol) in 3/1 mix of THF/water (100 ml). Add OsO4 (5.99 g, 0.59 mmol) and NaIO4 (3.82 g, 17.86 mmol). Stir the resulting suspension for 3 hr at room temperature. Quench with 1M solution of sodium thiosulfate (300 ml). Extract in ethyl acetate. Column separation affords 0.885 g (28.5%) of 4-(4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde.

Workup

  1. customQuench with 1M solution of sodium thiosulfate (300 ml)
  2. extractionExtract in ethyl acetate
  3. customColumn separation

Sources & evidence

ORD record
ord-a363ed10c1f44384974b2391b9a41b16
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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