Sodium borohydride → HCID 68908782, compound

HRID 217296Notes

Reaction equation

HRID 217296 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C[O:7][C:8]([CH2:10][C:11]1[CH:20]=[C:19]([C:21]#[N:22])[C:18]([Cl:23])=[CH:17][C:12]=1[C:13](OC)=[O:14])=O.COC(CC1C(Cl)=C(C#N)C=CC=1C(OC)=O)=O>O.O1CCCC1.C(O)C>[Cl:23][C:18]1[CH:17]=[C:12]([CH2:13][OH:14])[C:11]([CH2:10][CH2:8][OH:7])=[CH:20][C:19]=1[C:21]#[N:22]

Participants

8

Reactant 4

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 68906400HCID 68906400, compoundHCID 68906716HCID 68906716, compound

Product 1

HCID 68908782HCID 68908782, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Calcium chloride (0.33 g, 3 mmol) and sodium borohydride (0.23 g, 6 mmol) were added to a mixture (0.80 g, 3 mmol) of methyl 2-methoxycarbonylmethyl-4-cyano-5-chlorobenzoate and methyl 2-methoxycarbonylmethyl-4-cyano-3-chlorobenzoate in a mixed solution (1:1, 10 mL) of ethanol and tetrahydrofuran. The resulting mixture was stirred at room temperature overnight. Water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a 0.6:1 mixture (0.57 g, 89%) of the title compound and 2-chloro-3-(2-hydroxyethyl)-4-hydroxymethylbenzonitrile.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b39cd99ff1b245c4984cf6908c063167
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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