Sodium borohydride → [4-(Azidomethyl)phenyl]methanol

HRID 1509360Notes

Reaction equation

HRID 1509360 reaction equation
[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[BH4-].[Na+]>CO.C(OCC)(=O)C>[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 574448534-(Azidomethyl)benzaldehyde

Product 1

HCID 23132430[4-(Azidomethyl)phenyl]methanolYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Azide 4 (2.0 g, 12.4 mmol) was dissolved in MeOH (50 ml) and cooled to 0° C. before NaBH4 was added slowly and the reaction mixture was stirred for 1 hour, after which the solvent was evaporated. The residue obtained was dissolved in ethyl acetate (50 ml) and water (50 ml), the phases were separated and the organic phase was washed with water (100 ml), dried over Na2SO4, and evaporated to yield 5 as a clear oil (1.96 g, 12.0 mmol, 97%). Rf=0.45 (DCM); νmax=cm−1; 1H NMR (300 MHz, CDCl3) δ=7.40 (d, 3J(H,H) 8.2 Hz, 2H, ArCH α to CH2OH), 7.33 (d, 3J(H,H)=8.2 Hz, 2H, ArCH α to CH2N3), 4.71 (s, 2H, CH2OH), 4.34 (s, 2H, CH2N3), 1.80 (bs, 1H, OH); 13C NMR (75 MHz, CDCl3) δ=141.0 (ArCCH2OH), 134.7 (ArCCH2N3), 128.5 (ArCH α to CH2N3), 127.4 (ArCH α to CH2OH), 64.9 (CH2OH), 54.5 (CH2N3).

Workup

  1. additionwas added slowly
  2. customafter which the solvent was evaporated
  3. customThe residue obtained
  4. customwater (50 ml), the phases were separated
  5. washthe organic phase was washed with water (100 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-0dd7145c94284ab6b2a3b9f72b8f1bff
Source dataset
uspto-grants-2015_12
Patent number
US09222941B2

Reaction notes

Loading…