HCID 19978441, compound → HCID 19978430, compound

HRID 1089846Notes

Reaction equation

HRID 1089846 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[CH3:15])[CH:7]([C:16](O)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH3:15][C:12]1[C:13]2[C:14]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])[CH:7]([CH2:16][OH:17])[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 19978441HCID 19978441, compound

Product 1

HCID 19978430HCID 19978430, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4,5-dimethyl-9-fluorenecarboxylic acid (4.2 g, 17.8 mmol) in 100 mL of THF was Charged with IM THF solution of BH3 -THF complex (25.0 mL, 25.0 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched with water (100 mL) and HCl (3 mL). After addition of ethyl acetate (50 mL) the organic layer was separated and washed with 10% potassium carbonate solution, water, brine, dried dried over magnesium sulfate and evaporated to afford 4.5-dimethyl-9-fluorenemethanol (3.0 g, 75.3%).

Workup

  1. customthen quenched with water (100 mL) and HCl (3 mL)
  2. additionAfter addition of ethyl acetate (50 mL) the organic layer
  3. customwas separated
  4. washwashed with 10% potassium carbonate solution, water, brine
  5. customdried
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-84393285bab4433ab29b874bcfc837f9
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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