Lithium borohydride → HCID 66877106, compound

HRID 447848Notes

Reaction equation

HRID 447848 reaction equation
[CH:1]1([S:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11](OC)=[O:12])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+]>O1CCCC1CCO>[CH:1]1([S:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[CH2:11][OH:12])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66877458Methyl 2-(cyclopentylsulfonyl)benzoate

Product 1

HCID 66877106HCID 66877106, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Conditions

Temperature
60 °C

Procedure

(Step 2) To a solution of methyl 2-(cyclopentylsulfonyl)benzoate obtained in Step 1 (4.1 g) in tetrahydrofuran-ethanol (100 ml+10 ml) was added lithium borohydride (500 mg) at 0° C. The mixture was stirred at 60° C. for 3 hr, quenched with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure to give [2-(cyclopentylsulfonyl)phenyl]methanol (3.1 g).

Workup

  1. customquenched with 1N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-247ad7919d444f9f9ebcb809895a474d
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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