Water → (2S)-2-(3,4-dichlorophenyl)pent-4-en-1-ol

HRID 1533062Notes

Reaction equation

HRID 1533062 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:27])[C@H:15]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH2:16][CH:17]=[CH2:18])C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:26][C:21]1[CH:20]=[C:19]([C@@H:15]([CH2:14][OH:27])[CH2:16][CH:17]=[CH2:18])[CH:24]=[CH:23][C:22]=1[Cl:25]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 538341524(S)-Benzyl-3-(2(S)-(3,4-dichlorophenyl)pent-4-en-1-oyl)oxazolidin-2-one

Product 1

HCID 18392749(2S)-2-(3,4-dichlorophenyl)pent-4-en-1-olYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4(S)-Benzyl-3-(2(S)-(3,4-dichlorophenyl)pent-4-en-1-oyl)oxazolidin-2-one (30.32 g) (see Bioorganic and Medicinal Chemistry Letters, 3, 319, (1993)) was dissolved in if anhydrous tetrahydrofuran (400 ml), cooled in an ice-bath and lithium aluminium hydride (5.7 g) carefully added in two portions (exothermic reaction). The mixture was stirred at 0° C. for 20 minutes and then stirred at room temperature for 1 hour before being cooled to 0° C. Water (6 ml) was carefully added followed by 2N aqueous sodium hydroxide solution (6 ml) and fixrther water (12 ml). The mixture was stirred vigourously for 40 minutes and the resulting precipitate removed by filtration and washed with diethyl ether. The filtrate was collected and the organic and aqueous phases separated. The solvent was then removed from the organic phase under reduced pressure to give a yellow oil which was chromatographed on silica gel eluting with a solvent gradient of 4:1 changing to 4:0, by volume, dichloromethane:hexane to give 4(S)-(3,4-dichlorophenyl)-5-hydroxypent-1-ene (11.74 g) as an oil.

Workup

  1. temperaturecooled in an ice-bath
  2. stirringstirred at room temperature for 1 hour
  3. temperaturebefore being cooled to 0° C
  4. stirringThe mixture was stirred vigourously for 40 minutes
  5. customthe resulting precipitate removed by filtration
  6. washwashed with diethyl ether
  7. customThe filtrate was collected
  8. customthe organic and aqueous phases separated
  9. customThe solvent was then removed from the organic phase under reduced pressure
  10. customto give a yellow oil which
  11. customwas chromatographed on silica gel eluting with a solvent gradient of 4:1 changing to 4:0, by volume, dichloromethane

Sources & evidence

ORD record
ord-74fb94cc879b4369b776107263f3c6ee
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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