Hydrochloric Acid → methyl 5-tert-butylfuran-2-carboxylate

HRID 537749Notes

Reaction equation

HRID 537749 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]([O:12][CH3:13])=[O:11].[C:14](Br)([CH3:17])([CH3:16])[CH3:15].Cl>C(=S)=S>[C:14]([C:9]1[O:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10485t-Butyl bromideHCID 11902Methyl 2-furoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 250082methyl 5-tert-butylfuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

AlCl3 (25.4 g, 190 mmol) is added batchwise to methyl furan-2-carboxylate (20.0 g, 159 mmol) and tert.-butylbromide (21.4 mL, 190 mmol) in CS2 (200 mL) while cooling with ice and the mixture is stirred for 6 h at RT. The reaction mixture is poured onto ice water, mixed with conc. hydrochloric acid (25 mL) and stirred for 10 min. Then the aqueous phase is extracted 2× with 200 mL EA. The combined organic phase is dried on Na2SO4, filtered and evaporated down using the rotary evaporator. The methyl 5-tert.-butyl-furan-2-carboxylate thus obtained is used further without any additional purification steps.

Workup

  1. temperaturewhile cooling with ice
  2. additionThe reaction mixture is poured onto ice water
  3. stirringstirred for 10 min
  4. extractionThen the aqueous phase is extracted 2× with 200 mL EA
  5. customThe combined organic phase is dried on Na2SO4
  6. filtrationfiltered
  7. customevaporated down
  8. customthe rotary evaporator

Sources & evidence

ORD record
ord-2db3cf5d459d43328f9035965ebf1810
Source dataset
uspto-grants-2014_10
Patent number
US08865703B2

Reaction notes

Loading…