Lithium diisobutylpiperidinohydroaluminate (LDBPA) as a mild and efficient reducing agent for the conversion of ester to aldehyde

Bulletin of the Korean Chemical Society

Volumn 26, Issue 3, 2005, Pages 377-378

  Ahn, Jin Hee ^b   Song, Jeong In ^a   Ahn, Jeong Eun ^a   An, Duk Keun ^a  

^a Kangwon National University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

Aldehyde; Diisobutylaluminium hydride; Lithium diisobutylpiperidinohydroaluminate (LDBPA); Partial reduction; Piperidine

Indexed keywords

ALDEHYDE; ALUMINUM DERIVATIVE; BENZALDEHYDE; BENZOIC ACID ISOPROPYL ESTER; BENZOIC ACID PHENYL ESTER; CINNAMIC ACID ETHYL ESTER; DIISOBUTYLALUMINUM HYDRIDE; ESTER; ETHYL BENZOATE; HEXANOIC ACID ETHYL ESTER; ISOPROPYL CAPROATE; LITHIUM DIISOBUTYLPIPERIDINOHYDROALUMINATE; METHYL 3 CHLOROBENZOATE; METHYL 3,4 DIMETHOXYBENZOATE; PIPERIDINE DERIVATIVE; REDUCING AGENT; TERT BUTYL BENZOATE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; UNDECANOIC ACID ETHYL ESTER;

ARTICLE; LOW TEMPERATURE; REACTION ANALYSIS; REDUCTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 16444365836     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2005.26.3.377     Document Type: Article

References (11)

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10. The following procedure for the preparation of LDBPA is illustrative. To a solution of piperidine (0.99 mL, 10 mmol) in THF (2.76 mL) was added n-butyllithium (6.25 mL, 1.6 M in hexane, 10 mmol) at 0 °C. After being stirred for 1 h at room temperature, to this added dropwise DIBAH (10 mL, 1.0 M in hexane, 10 mmol) at 0 °C and the mixture was stirred for 1 h at room temperature. The result was clear colorless solution.
11. The following procedure for the reduction of ethyl benzoate with LDBPA is representative. To a solution of ethyl benzoate (0.07 mL, 0.5 mmol) in THF (5 mL) containing naphthalene as an internal standard was added LDBPA (1.5 mL, 0.5 M in THF-hexane) at 0 °C. After 3h, the reaction mixture was hydrolyzed with 5 mL of 1 N HCl (aq) and the product was extracted with 10 mL of diethyl ether. The ether layer was dried over anhydrous potassium carbonate. GC analysis showed an 83% yield of benzaldehyde.