Sodium hydride → HCID 14484449, compound

HRID 1586900Notes

Reaction equation

HRID 1586900 reaction equation
[H-].[Na+].C([C:5]1([O:16]C(=O)C)[CH2:10][CH:9]=[CH:8][CH2:7][CH:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])C>C(O)C>[OH:16][C@@H:5]1[CH2:10][CH:9]=[CH:8][CH2:7][C@H:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19760170HCID 19760170, compound

Product 1

HCID 14484449HCID 14484449, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydride (200 mg) was added to a mixture of the cis and trans isomers of ethyl 1-acetoxy-2-carboethoxycyclohex-4-ene (1.60 g, 7.55 mmol) in absolute ethanol (50 ml), and the mixture was stirred for 1 hour at RT. The reaction mixture was neutralized with Dowex W 50 cation exchange resin (acid form), the resin removed by filtration, the solvents removed under vacuum, and the residue chromatographed on silica gel (hexane:EtOAc 7:3, Rf=0.40) to yield 1.2 g (94%) trans 1-hydroxy-2-carboethoxycyclohex-4-ene (IR CCl4, 1732 cm-1).

Workup

  1. customthe resin removed by filtration
  2. customthe solvents removed under vacuum
  3. customthe residue chromatographed on silica gel (hexane:EtOAc 7:3, Rf=0.40)

Sources & evidence

ORD record
ord-f17f46a9894a43a08ba772352e62df1a
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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