HCID 19978414, compound → HCID 19978413, compound

HRID 1089850Notes

Reaction equation

HRID 1089850 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:16]2[CH:15]([C:17](O)=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1>C1COCC1>[CH3:1][O:2][CH2:3][C:4]1[C:16]2[CH:15]([CH2:17][OH:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 19978414HCID 19978414, compound

Product 1

HCID 19978413HCID 19978413, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methoxymethyl-9-fluorenecarboxylic acid (3.4 g, 13.4 mmol) in 100 mL of THF was charged with 1M THF solution of BH3 -THF complex (30.0 mL, 30.0 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched with water (100 mL). The organic layer was washed with 10% potassium carbonate solution, water, brine, dried over magnesium sulfate and evaporated. Short path chromatography of the residual oil (silica, 25% ethyl acetate in hexane) afforded 1-methoxymethyl-9-fluorenemethanol (2.6 g, 79.9%).

Workup

  1. customthen quenched with water (100 mL)
  2. washThe organic layer was washed with 10% potassium carbonate solution, water, brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3b6c7f74a6a24a3c8edec3b1b4feb605
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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