Hydrochloric Acid → HCID 67440088, compound

HRID 1471473Notes

Reaction equation

HRID 1471473 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([B:20]3[O:24][C:23](C)(C)C(C)(C)[O:21]3)=[C:16](C=O)[CH:15]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].[BH4-].[Na+].Cl>CO>[C:1]([C:3]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]3[B:20]([OH:21])[O:24][CH2:23][C:16]=3[CH:15]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636412HCID 86636412, compound

Product 1

HCID 67440088HCID 67440088, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-cyano-5-(3-formyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzoate (15.7 g) in methanol (150 mL) was added sodium borohydride (646 mg, 17.0 mmol) portionwise at 0° C. The mixture was stirred at room temperature for 1 h. The mixture was acidified with 6 M HCl, and extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (6:4 to 4:6 hexane/ethyl acetate) followed by recrystallization from methanol/water to give 5-(4-cyano-3-methoxycarbonylphenoxy)-1-hydroxy-2,1-benzoxaborole (6.34 g, 62%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel chromatography (6:4 to 4:6 hexane/ethyl acetate)
  6. customfollowed by recrystallization from methanol/water

Sources & evidence

ORD record
ord-7cfc6c4a229842258ee5b75d8dbd215e
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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