Tetrahydrofuran → 2-(3-Chlorophenyl)-2-methylpropanal

HRID 83866Notes

Reaction equation

HRID 83866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:5]=[CH:6][CH:7]=1.CC(C[AlH]CC(C)C)C.C1C[O:25]CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 213298602-(3-Chlorophenyl)-2-methylpropanenitrile

Product 1

HCID 820751242-(3-Chlorophenyl)-2-methylpropanalYield 88%

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(3-chlorophenyl)-2-methylpropanenitrile (5.3 g, 29.2 mmol) in THF (80 mL, anhyd) at −78° C. was added dropwise DIBAL-H (1M in toluene, 87 mL, 87 mmol, 3 eq) over 2 h. After stirring 30 min at −78° C., the reaction mixture was allowed to warm to room temperature, quenched with 2N HCl and extracted with EtOAc. The combined extracts were dried over MgSO4 and evaporated in vacuo to give 2-(3-chlorophenyl)-2-methylpropanal (4.6 g, 88%). 1H NMR (400 MHz, CDCl3) δ 9.48 (s, 1H), 7.32 (m, 3H), 7.14 (m, 1H), 1.51 (s, 6H).

Workup

  1. temperatureto warm to room temperature
  2. customquenched with 2N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined extracts were dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e1dcd480e6fe4289854a4fda6440d0f1
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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