3-Hydroxybenzaldehyde → HCID 18617256, compound

HRID 276083Notes

Reaction equation

HRID 276083 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]1([C:16]2[O:17][CH:18]=[C:19]([CH2:21][CH2:22]O)[N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:10]1([C:16]2[O:17][CH:18]=[C:19]([CH2:21][CH2:22][O:1][C:2]3[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=3)[CH:5]=[O:6])[N:20]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10487882HCID 10487882, compound

Product 1

HCID 18617256HCID 18617256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.00 g (81.89 mmoles) of 3-hydroxybenzaldehyde, 15.49 g (81.89 mmoles) of 2-(2-phenyl-4-oxazolyl)ethanol, and 21.48 g (81.89 mmoles) of triphenylphosphine were dried under vacuum and combined with 200 mL THF under N2. The mixture was treated with 16.12 mL (81.89 mmoles) of diisopropylazodicarboxylate added dropwise over 0.25 hr resulting in a mild exotherm. After stirring for 24 hr at ambient temperature, the crude reaction mixture was concentrated under reduced pressure to a viscous amber oil. The oil was diluted in 300 mL EtOAc, washed with 2.5 N NaOH (3×200 mL), H2O (2×300), and brine 300 mL. The combined organics were dried over MgSO4 and concentrated under reduced pressure again to a viscous amber oil. The reaction mixture was separated using silica gel column chromatography (6:1 Hex:EtOAc) from which the product was recovered and then recrystallized from iprOH to afford 15.10 g (63.10%.) of white crystalline solid, m.p. 51-53° C.

Workup

  1. additionadded dropwise over 0.25 hr
  2. customresulting in a mild exotherm
  3. customthe crude reaction mixture
  4. concentrationwas concentrated under reduced pressure to a viscous amber oil
  5. additionThe oil was diluted in 300 mL EtOAc
  6. washwashed with 2.5 N NaOH (3×200 mL), H2O (2×300), and brine 300 mL
  7. dry with materialThe combined organics were dried over MgSO4
  8. concentrationconcentrated under reduced pressure again to a viscous amber oil
  9. customThe reaction mixture was separated
  10. customwas recovered
  11. customrecrystallized from iprOH
  12. customto afford 15.10 g (63.10%.) of white crystalline solid, m.p. 51-53° C.

Sources & evidence

ORD record
ord-d60c110869c941578e50eafdc3b87b34
Source dataset
uspto-grants-2002_03
Patent number
US06353027B1

Reaction notes

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