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1,2-Dimethoxyethane → Methyl 5-(4-fluorophenyl)-2-(methoxymethyl)furan-3-carboxylate

HRID 1877292
Notes
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Reaction equation

HRID 1877292 reaction equation
Br[C:2]1[O:6][C:5]([CH2:7][O:8][CH3:9])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[O:6][C:5]([CH2:7][O:8][CH3:9])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=2)=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 68509863Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate

Product 1

HCID 68511619Methyl 5-(4-fluorophenyl)-2-(methoxymethyl)furan-3-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

Procedure

A mixture of methyl 5-bromo-2-(methoxymethyl)furan-3-carboxylate (2.5 g), 4-fluorophenylboronic acid (1.7 g), tetrakis(triphenylphosphine)palladium(0) (0.6 g), 2N aqueous sodium carbonate solution (14 mL) and 1,2-dimethoxyethane (30 mL) was stirred under reflux overnight under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 25% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (2.4 g, 91%) as a white crystal.

Workup

  1. temperatureunder reflux overnight under an argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 25% ethyl acetate/hexane)
  7. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-aa29a57230304c108c06e38203fc1ee5
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309580B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes