Lithium borohydride → HCID 22145918, compound

HRID 1092814Notes

Reaction equation

HRID 1092814 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[CH:5]=[C:4]([Cl:13])[C:3]=1[NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:17]=1.[BH4-].[Li+]>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:13])[C:3]=1[NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH:17]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 22145785HCID 22145785, compound

Product 1

HCID 22145918HCID 22145918, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of N-(2,6-dichloro-4-ethoxycarbonylphenyl)-3-cyclopentyloxy-4-methoxybenzamide (6.1 g) in dry tetrahydrofuran (80 mL) at room temperature under argon is treated dropwise with a solution of lithium borohydride in tetrahydrofuran (115 mL; 2 M). The mixture is stirred overnight and then it is treated portionwise with saturated brine (200 mL) and stirred for 30 minutes. The organic layer is then washed with water, dried over magnesium sulfate and evaporated. The resulting residue is subjected to flash chromatography on silica gel, to give N-(2,6-dichloro-4-hydroxymethylphenyl)-3-cyclopentyloxy-4-methoxybenzamide (4.4 g), m.p. 174-176° C. [Elemental analysis: C, 57.1; H, 5.4; N, 2.9%; calculated C20H21O4NCl2:0.5H2O: C, 57.3; H, 5.3; N, 3.3%]

Workup

  1. stirringstirred for 30 minutes
  2. washThe organic layer is then washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-47c5577e1fc04c7aacc53ec3b97eeae7
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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