Sodium borohydride → HCID 67441871, compound

HRID 1471491Notes

Reaction equation

HRID 1471491 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[CH:15]=[O:16])=[CH:4][C:3]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[CH2:15][OH:16])=[CH:4][C:3]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86636416HCID 86636416, compound

Product 1

HCID 67441871HCID 67441871, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[4-bromo-3-(2-tetrahydropyranyloxymethyl)phenoxy]-3-formylbenzonitrile obtained in Example 19w (D23) (14.6 g, 34.9 mmol) in methanol (100 mL) was added sodium borohydride (664 mg g, 17.5 mmol) portionwise at 0° C., and the mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to a half volume, and the mixture was poured into ethyl acetate/water. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-[4-bromo-3-(2-tetrahydropyranyloxymethyl)phenoxy]-3-(hydroxymethyl)benzonitrile (14.6 g, 100%).

Workup

  1. customThe solvent was removed under reduced pressure to a half volume
  2. additionthe mixture was poured into ethyl acetate/water
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-034256b5e011423fb428a0e2e7e30c01
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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