Lithium borohydride → HCID 58754169, compound

HRID 2042913Notes

Reaction equation

HRID 2042913 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[BH4-].[Li+]>C1COCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH2:7][OH:8])[CH:12]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 44829046Ethyl 5-iodo-2-methylbenzoate

Product 1

HCID 58754169HCID 58754169, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ester 4 (41.0 g, 141 mmol) in THF (300 mL) was added lithium borohydride (2.0 M in THF, 212 mL). The reaction mixture was refluxed overnight. After cooling to 0° C., the reaction was quenched by addition of aq. saturated NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to yield the titled compound (34.0 g, 97%) as a white solid, which was carried on to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customthe reaction was quenched by addition of aq. saturated NH4Cl solution
  3. additionThe mixture was diluted with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-1f5ef8088b5e4849be5c0b104958cf58
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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