(Z)-Benzaldehyde oxime → HCID 67099702, compound

HRID 1868880Notes

Reaction equation

HRID 1868880 reaction equation
C(=N[OH:9])C1C=CC=CC=1.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:23](OCC)=[O:24])[CH2:22][CH2:21][CH2:20]2)=[C:15]([C:28]#[C:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:14]=1>CN(C=O)C.O1CCOCC1>[Cl:12][C:13]1[CH:14]=[C:15]2[C:16](=[CH:17][CH:18]=1)[C:19]1([CH2:22][CH2:21][CH2:20]1)[C:23](=[O:24])[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]2[OH:9]

Participants

6

Reactant 3

HCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 67099864HCID 67099864, compound

Product 1

HCID 67099702HCID 67099702, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzaldehyde oxime (174 mg, 1434 μmol) in DMF (7 mL) was added to a stirred suspension of NaH (60% dispersion in mineral oil (57 mg, 1434 μmol)) in dioxane (7 mL) under a N2 atmosphere. The mixture was stirred for approximately 30 minutes before being cooled to 0° C. Ethyl 1-(4-chloro-2-(3-ethoxy-3-oxoprop-1-ynyl)phenyl)cyclobutanecarboxylate (400 mg, 1195 μmol) in DMF (7 mL) was added via syringe, and the reaction was stirred at 0° C. for 1 hour. The reaction was quenched with water, and extracted with EtOAc. The aqueous layer was separated and brought to a pH of about 4 with 10% HCl and extracted again with EtOAc (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give an orange oil. The crude oil was purified by silica flash chromatography (0-20% EtOAc/hexane) to give the desired compound as a white solid (155 mg). MS (m/e)=307.1 (M+H)+.

Workup

  1. stirringthe reaction was stirred at 0° C. for 1 hour
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe aqueous layer was separated
  5. extractionextracted again with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an orange oil
  9. customThe crude oil was purified by silica flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-b5f10770ddf34827bcb827340852fedd
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…