Dichloromethane → HCID 59589352, compound

HRID 577012Notes

Reaction equation

HRID 577012 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].ClCCl>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 59589465HCID 59589465, compound

Product 1

HCID 59589352HCID 59589352, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chloro-5-[(diethylamino)methyl]benzoate (3.97 g, 15.5 mmol) in anhydrous THF (100 mL) was added a solution of diisobutylaluminium hydride (1 M in toluene, 35 mL, 35 mmol). The reaction mixture was stirred at room temperature for 90 minutes. A Rochelle's salt solution (200 mL) and dichloromethane (200 mL) were added. The resultant mixture was stirred at room temperature for 2 hours. The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording {2-chloro-5-[(diethylamino)methyl]phenyl}methanol (3.0 mg, 85% yield). The product was used without further purification.

Workup

  1. customThe organic layer was recovered
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6fc69590fd574646930c6c9264b3eabe
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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