Diethyl Ether → HCID 62498593, compound

HRID 1366802

Reaction equation

HRID 1366802 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C[Mg+].[Br-].[CH3:18]COCC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([CH:13]([OH:14])[CH3:18])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6098225-(3-Chlorophenyl)furfuralHCID 178418689HCID 178418689, compound

Product 1

HCID 62498593HCID 62498593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-chlorophenyl)furan-2-carbaldehyde (1.0 equiv.) in THF at 0° C. was added MeMgBr in ether (3.0 equiv.) and stirred for 45 min. The reaction was quenched with water, diluted with ether and filtered through Celite. The organic layer was separated and washed with brine, dried over MgSO4, and concentrated to give the 1-[5-(3-chlorophenyl)-2-furyl]ethan-1-ol.

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with ether
  3. filtrationfiltered through Celite
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef510c6e17114ee2bb54dac234e3a116
Source dataset
uspto-grants-2011_02
Patent number
US07893096B2

Linked notes

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