Diethyl Ether → HCID 20536101, compound

HRID 1855797Notes

Reaction equation

HRID 1855797 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[CH2:7]O.[BrH:11].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOCC>ClCCl>[Br-:11].[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[CH2:7][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 80811Triphenylphosphonium bromideHCID 20256465HCID 20256465, compound

Product 1

HCID 20536101HCID 20536101, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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. customthe solids formed
  2. customwere crystallized from a 1:5 parts by volume mixture of methanol and ethylacetate

Sources & evidence

ORD record
ord-b77f99c4ed164a34a209d9094d63be2a
Source dataset
uspto-grants-1980_08
Patent number
US04216312

Reaction notes

Loading…