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

HRID 1044782Notes

Reaction equation

HRID 1044782 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

Conditions

Temperature
0 °C

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 (1.84 g, 9.59 mmol) in MeOH (20 mL) was added NaBH4 (456 mg, 12.05 mmol in four portions). The reaction mixture was then stirred for 1 h at 0° C. 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 pale yellow oil. TLC:rf (4:1 hept-EA)=0.12. LC-MS-conditions 02: tR=0.74 min.

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-33f59c34cd6941688d5d17628315b61b
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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