Nitrogen → [3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl]-methanol

HRID 42759Notes

Reaction equation

HRID 42759 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[O:8][CH2:7][CH2:6][O:5]1.[BH4-].[Na+].O>CO>[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][CH:16]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 4311764Sodium borohydrideHCID 10607757Benzaldehyde, 3-(2-methyl-1,3-dioxolan-2-yl)-

Product 1

HCID 66820167[3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a ice-cold solution of 3-(2-methyl-[1,3]dioxolan-2-yl)-benzaldehyde (896 mg, 4.66 mmol) in MeOH (10.0 mL) was added NaBH4 (228 mg, 5.79 mmol in four equal portion). The reaction mixture was then stirred for 1 h at rt. Water was added and the mixture was extracted twice with EA. The combined org. extracts were washed with brine, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a colorless oil: TLC:rf (50:50 hept-EA)=0.28. LC-MS-conditions 02: tR=0.74 min; [M+H]+=195.71.

Workup

  1. extractionthe mixture was extracted twice with EA
  2. washextracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-42b730f5f9c4460d818e128e3b46e153
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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