2-(2-Hydroxyethyl)pyridine → 2-Hydroxy-3-[2-(2-pyridinyl)ethoxy]benzaldehyde

HRID 983788Notes

Reaction equation

HRID 983788 reaction equation
C([O:8][C:9]1[C:16](O)=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[OH:8][C:9]1[C:16]([O:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 76752-(2-Hydroxyethyl)pyridineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 130703912-(Benzyloxy)-3-hydroxybenzaldehyde

Product 1

HCID 225570022-Hydroxy-3-[2-(2-pyridinyl)ethoxy]benzaldehydeYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-benzyloxy-3-hydroxy-benzaldehyde 16 (0.30 g, 1.3 mmol), triphenylphosphine (0.41 g, 1.6 mmol) and 2-(2-hydroxyethyl)pyridine (0.18 ml, 1.6 mmol) were stirred in THF (15 ml), followed by the addition of DEAD (0.25 ml, 1.6 mmol). After stirring for 12 h, the reaction mixture is partitioned between ethyl acetate (200 ml) and saturated aqueous sodium hydrogen carbonate (200 ml). The organic layer is separated, dried (MgSO4), filtered and concentrated to give a brown oil. The brown oil is purified by flash chromatography (50% ethyl acetate/hexanes) to afford 0.29 g (66%) of 2-hydroxy-3-(2-pyridin-2-ylethoxy)benzaldehyde 17 as a light yellow solid.

Workup

  1. customthe reaction mixture is partitioned between ethyl acetate (200 ml) and saturated aqueous sodium hydrogen carbonate (200 ml)
  2. customThe organic layer is separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown oil
  7. customThe brown oil is purified by flash chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-390ab00d03084703aac17634387f7055
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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