Carbon Dioxide → (5-Chloro-6-iodo-3-pyridinyl)methanol
Reaction equation
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([C:18](OCC)=[O:19])[CH:14]=[N:15][C:16]=1[I:17].C(=O)=O.C(C(C(C([O-])=O)O)O)([O-])=O>C1COCC1.CCOC(C)=O>[Cl:10][C:11]1[CH:12]=[C:13]([CH2:18][OH:19])[CH:14]=[N:15][C:16]=1[I:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
DIBAL-H (3.37 ml, 3.37 mmol) was slowly added to a solution of ethyl 5-chloro-6-iodo-3-pyridinecarboxylate (500 mg, 1.605 mmol) in THF (10 ml) at −78° C. The solution turned yellow and was stirred at that temperature for 3 h and then still in the dry-ice bath allowed to slowly attain room temperature overnight. Next morning, TLC showed starting material remaining. The solution was cooled to −78° C. and DIBAL-H (3.37 ml, 3.37 mmol) was added. 3 h later it was allowed to warm to room temperature and after 2 h starting material was still observed. More DIBAL-H (6.74 ml) was added and the solution stirred at room temperature overnight. Full conversion was observed. Saturated, aqueous NaK-tartrate solution and EtOAc were added. Extraction, drying (MgSO4), filtration, and concentration afforded (5-chloro-6-iodo-3-pyridinyl)methanol (393 mg, 91%) as a brown solid pure enough to be used in the next step.
Workup
- customallowed to slowly attain room temperature overnight
- custom3 h later it
- temperatureto warm to room temperature and after 2 h
- stirringthe solution stirred at room temperature overnight
- extractionExtraction
- customdrying
- filtration(MgSO4), filtration, and concentration
Sources & evidence
- ORD record
- ord-6c79c72bfce44b04b749a816367f9690
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097628B2
Reaction notes
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