4-Nitrobenzaldehyde → HCID 12808781, compound

HRID 2107365Notes

Reaction equation

HRID 2107365 reaction equation
[Li]CCCC.[N+:6]([CH2:9][CH2:10][CH3:11])([O-:8])=[O:7].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>C1COCC1.C(Cl)Cl>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([CH:19]([OH:20])[CH:9]([N+:6]([O-:8])=[O:7])[CH2:10][CH3:11])=[CH:21][CH:22]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 6049Ethylenediaminetetraacetic AcidHCID 79031-NitropropaneHCID 178418339Butyllithium

Product 1

HCID 12808781HCID 12808781, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (1.6 M in hexane, 6.24 mL) was added dropwise with stirring to a solution of nitropropane (0.9mL, 10mmol) in THF (12 mL) at -78° C. After 15 minutes a solution of TiCl3 (OPriso) (5 mmol) in THF (2 mL) and CH2Cl2 (3 mL) solution was added. After a further 15 minutes 4-nitrobenzaldehyde (0.75 mL, 5 mmol) in CH2Cl2 (4 mL) was added and the mixture allowed to warm up to room temperature (~30 min). Stirring was continued for a further 3.5 hours at room temperature and the mixture was quenched with an aqueous slurry of disodium EDTA (1.86 g, 5mmol) and extracted with Et2O (3×75 mL). The combined Et2O fractions were washed with dilute hydrochloric acid (2 M, 75 mL), aqueous sodium bicarbonate (75 mL) and water (75 mL), dried and evaporated in vacuo. Flash column chromatrography [Si2, hexane:Et2O, 3:1 v/v] gave 1-(4-nitrophenyl)-2-nitro-butan-1-ol (0.86 g, 72%) Erythro:threo ratio 7:1.

Workup

  1. extractionextracted with Et2O (3×75 mL)
  2. washThe combined Et2O fractions were washed with dilute hydrochloric acid (2 M, 75 mL), aqueous sodium bicarbonate (75 mL) and water (75 mL)
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d0d5e09ac0394ddaa5c17b9144bf177e
Source dataset
uspto-grants-1990_06
Patent number
US04933505

Reaction notes

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