Lithium borohydride → 2-(3-Nitrophenyl)propan-1-ol

HRID 1179600Notes

Reaction equation

HRID 1179600 reaction equation
[BH4-].[Li+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]([CH3:17])[C:13](OC)=[O:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]>C1COCC1>[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]([CH3:17])[CH2:13][OH:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 13054272Methyl 2-(3-nitrophenyl)propanoate

Product 1

HCID 226740402-(3-Nitrophenyl)propan-1-olYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium borohydride (2M, THF, 2.0 equiv. 3.4 ml) was added to a solution of methyl 2-(3-nitrophenyl)propanoate (0.7 g) in THF. The resulting mixture was stirred for 18 hours then concentrated and poured into hydrochloric acid (10%) at 0 □C. The mixture was extracted with ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated to afford the title compound as yellow oil (0.610 g, 100% yield).

Workup

  1. concentrationthen concentrated
  2. additionpoured into hydrochloric acid (10%) at 0 □C
  3. extractionThe mixture was extracted with ether
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-042b03b82df347ffb79d42228abc49f1
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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