Lithium borohydride → HCID 22145918, compound

HRID 993265Notes

Reaction equation

HRID 993265 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-4967412fdff34006b42b3a65c79b2b48
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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