Sulfuric acid magnesium salt (1:1) → HCID 20256465, compound

HRID 1855796Notes

Reaction equation

HRID 1855796 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:13])=[C:5]([CH3:12])[C:6]=1[C:7](OCC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC>[CH3:1][C:2]1[O:3][C:4]([CH3:13])=[C:5]([CH3:12])[C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24436Sodium SulfateHCID 12346982Ethyl 2,4,5-trimethylfuran-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20256465HCID 20256465, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,4,5-Trimethyl-3-carbethoxyfuran (40 g.) prepared in accordance with Helv. Chim. Acta., v. 15, 1112 (1932), was dissolved in ether (200 ml.) and added to a cooled slurry of lithium aluminum hydride (10 g.) in ether (200 ml.) After stirring a further 16 hours at room temperature a saturated, aqueous solution of sodium sulfate was added followed by the addition of magnesium sulfate (50 g.). The solids were filtered off and the solvents were concentrated to give crude alcohol, 2,4,5-trimethyl-3-hydroxymethyl furan (31 g.). A solution of this alcohol (4.2 g.) in dichloromethan (10 ml.) was added to a cooled slurry of triphenylphosphine hydrobromide (10 g.) in dichloromethane (40 ml.) and then left at room temperature for 15 minutes. Ether was then added and the solids formed were crystallized from a 1:5 parts by volume mixture of methanol and ethylacetate to give pure (2,4,5-trimethyl-3-furyl) methyl triphenylphosphonium bromide (10.2 g.) m.p. 223°-224°.

Workup

  1. additionwas added
  2. filtrationThe solids were filtered off
  3. concentrationthe solvents were concentrated

Sources & evidence

ORD record
ord-d5451e75134040829f12dd6019184af1
Source dataset
uspto-grants-1980_08
Patent number
US04216312

Reaction notes

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