Sodium borohydride → HCID 28963963, compound

HRID 1667599Notes

Reaction equation

HRID 1667599 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:3])[CH3:2].[BH4-].[Na+]>CCCCCC>[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[CH2:7][OH:8])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 115575382-isopropoxy-5-nitrobenzaldehyde

Product 1

HCID 28963963HCID 28963963, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

To 8A (210 mg, 1.0 mmol) in hexane (10 mL) was added sodium borohydride (1 mg, 0.30 mmol) and silica gel (0.50 g). The mixture was degassed with Ar for 3 min, then stirred at 40° C. for 3 h under Ar. The reaction was filtered, concentrated and purified via silica gel chromatography (0-20% ethyl acetate/hexane) to provide 8B (195 mg, 92%). LC-MS: 212.19 (M+H)+.

Workup

  1. customThe mixture was degassed with Ar for 3 min
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified via silica gel chromatography (0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6f9b6963ac0342b5bcb5a98e5ef1165c
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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