Hydrochloric Acid → 2-Furanyl-di-(2-methoxyphenyl)methanol

HRID 32854

Reaction equation

HRID 32854 reaction equation
CO[C:3]([C:5]1[O:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Mg]Br.[C:20](=[O:23])(O)[O-].[Na+].Cl>C1COCC1>[O:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:23][CH3:20])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH3:10])[OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11902Methyl 2-furoateHCID 516892Sodium BicarbonateHCID 178489560HCID 178489560, compound

Product 1

HCID 230702572-Furanyl-di-(2-methoxyphenyl)methanolYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl-2-furoate (1.58 g, 0.0125 mol) was dissolved in 100 mL of dry THF. A dropping funnel containing 50 mL of a 0.5 M solution of 2-methoxyphenylmagnesium bromide in THF (Aldrich) was attached to the reaction flask and the system was purged with argon. The reaction flask was submerged in an ice bath for 5 minutes, at which time the Grignard solution was added drop-wise over 15 minutes. After addition was complete, the reaction was allowed to warm to room temperature and was stirred overnight. A brown solution resulted. This solution was added to 150 g crushed ice and the slush was stirred with ˜0.5 g sodium bicarbonate during drop-wise addition of conc. HCl. A lavender color was observed upon addition of acid, which was continued until effervescence was observed. The resulting neutral suspension was extracted into ˜400 mL EtOAc and the organic layer was dried over MgSO4. Removal of solvent in vacuo gave a clear/yellow oil. The oil was purified by silica gel column chromatography and the product eluted using a 50:50 (vol:vol) mixture of EtOAc:hexanes. The purified product was evaporated to a solid gum yielding 3.1 grams/82% yield. The product was characterized by HPLC, 1H NMR, and FAB mass spectroscopy FAB+311 m/e.

Workup

  1. customthe system was purged with argon
  2. additionthe Grignard solution was added drop-wise over 15 minutes
  3. additionAfter addition
  4. customA brown solution resulted
  5. additionThis solution was added to 150 g
  6. customcrushed ice
  7. additionA lavender color was observed upon addition of acid, which
  8. extractionThe resulting neutral suspension was extracted into ˜400 mL EtOAc
  9. dry with materialthe organic layer was dried over MgSO4
  10. customRemoval of solvent in vacuo
  11. customgave a clear/yellow oil
  12. customThe oil was purified by silica gel column chromatography
  13. washthe product eluted
  14. additiona 50:50 (vol:vol) mixture of EtOAc
  15. customThe purified product was evaporated to a solid gum
  16. customyielding 3.1 grams/82% yield

Sources & evidence

ORD record
ord-6e2b992b32604cfc94d55fb79d9b0d97
Source dataset
uspto-grants-2008_09
Patent number
US07427679B2

Linked notes

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