Sodium Bicarbonate → 3-[2-(Methyloxy)ethyl]-1-naphthalenecarbaldehyde

HRID 337602Notes

Reaction equation

HRID 337602 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:15]=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66895342{3-[2-(Methyloxy)ethyl]-1-naphthalenyl}methanol

Product 1

HCID 866516723-[2-(Methyloxy)ethyl]-1-naphthalenecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of {3-[2-(methyloxy)ethyl]-1-naphthalenyl}methanol (1 eq.) from the previous step and sodium bicarbonate (1.1 eq.) in dichloromethane (0.1 M) was added DMP (1.1 eq.) at 0° C. The resulting mixture was stirred at RT for 2 h before it was quenched with sat. aq. NaHSO3 and then extracted with Et2O. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc 1:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. additionwas added DMP (1.1 eq.) at 0° C
  2. customwas quenched with sat. aq. NaHSO3
  3. extractionextracted with Et2O
  4. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc 1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-cc7ad9d9dc9a4e9fbc25b9793b22b79e
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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