HCID 11299024, compound → 2-Methyl-2-(4-nitrophenyl)propan-1-ol

HRID 238514Notes

Reaction equation

HRID 238514 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([CH3:7])[C:3](OC)=[O:4]>C1COCC1>[CH3:7][C:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([CH3:1])[CH2:3][OH:4]

Participants

3

Reactant 1

HCID 11299024HCID 11299024, compound

Product 1

HCID 222492792-Methyl-2-(4-nitrophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of methyl 2-methyl-2-(4-nitrophenyl)propionate (5.32 g, 23.8 mmol, Step A) in THF (200 mL) at 0° C. was added a solution of BH3 1M in THF (25.8 mL, 45.8 mmol). The reaction was stirred at RT overnight and quenched with MeOH. THF was evaporated under reduced pressure and the residue was diluted in EtOAc and aqueous 1M HCl was added. The mixture was extracted with EtOAc, the organic layer was dried over MgSO4 and evaporated under reduced pressure. The product was purified by flash chromatography using 40% EtOAc-hexane to give the title compound as a yellow solid.

Workup

  1. customquenched with MeOH
  2. customTHF was evaporated under reduced pressure
  3. additionthe residue was diluted in EtOAc
  4. additionaqueous 1M HCl was added
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe organic layer was dried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-81d034130e0a4b889ec7d52cf199769d
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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