Sodium hydride → HCID 76739653, compound

HRID 2189061Notes

Reaction equation

HRID 2189061 reaction equation
[C@H:1]1([OH:7])[CH:5]=[CH:4][C@@H:3]([OH:6])[CH2:2]1.[H-].[Na+].[C:10]([O:14][C:15](=[O:18])[CH2:16]Br)([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C.C1COCC1>[C:10]([O:14][C:15](=[O:18])[CH2:16][O:6][CH:3]1[CH2:2][CH:1]([OH:7])[CH:5]=[CH:4]1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 10148988rel-(1R,3S)-4-Cyclopentene-1,3-diol

Product 1

HCID 76739653HCID 76739653, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2.0 g (20 mmol) of cis-4-cyclopentene-1,3-diol in 1.5 ml of DMF and 15 ml of THF and, at 0° C., add 799 mg (60% strength, approx. 20 mmol) of sodium hydride in portions. After the end of the addition, warm the mixture to RT and stir at RT for a further 1 h, before adding 2.7 ml (18.2 mmol) of bromoacetic acid tert-butyl ester. Then stir the mixture at RT overnight. Then add water, extract with dichloromethane, wash the organic phase with satd. sodium chloride solution, concentrate under reduced pressure and dry the residue under high vacuum. Isolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→2:1). 1.10 g (25.6% of theory) of the target compound are obtained.

Workup

  1. additionAfter the end of the addition
  2. stirringThen stir the mixture at RT overnight
  3. extractionThen add water, extract with dichloromethane
  4. washwash the organic phase with satd
  5. concentrationsodium chloride solution, concentrate under reduced pressure
  6. customdry the residue under high vacuum
  7. customIsolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→2:1)
  8. custom1.10 g (25.6% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-e53ea661c1784d0d83c7b2e62c186668
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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