Formaldehyde → HCID 22117513, compound

HRID 1275792Notes

Reaction equation

HRID 1275792 reaction equation
[C:1]1([CH:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH2:25]=[O:26]>C1COCC1>[OH:26][CH2:25][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 130919H-fluorene, 9-phenyl-HCID 178418339Butyllithium

Product 1

HCID 22117513HCID 22117513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 9-phenylfluorene (13.6 mmol) in THF (40 mL) is added nBuLi (1.2 eq) dropwise at 0° C. under an argon atmosphere. The resulting mixture is stirred at 0° C. for 30 min. Paraformaldehyde (1.2 eq) is added in one portion, and the resulting mixture is allowed to stir at room temperature overnight. The reaction mixture is quenched with saturated NH4Cl solution. The resulting mixture is extracted with EtOAc. The EtOAc layer is dried (Na2SO4) and concentrated in vacuo. The concentrate is purified by flash chromatography on silica gel eluting with hexanes-ethyl acetate to isolate the alcohol.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe reaction mixture is quenched with saturated NH4Cl solution
  3. extractionThe resulting mixture is extracted with EtOAc
  4. dry with materialThe EtOAc layer is dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe concentrate is purified by flash chromatography on silica gel eluting with hexanes-ethyl acetate

Sources & evidence

ORD record
ord-0d578cf4578b4649b981cec4ebadadad
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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