3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 19707442, compound

HRID 726754Notes

Reaction equation

HRID 726754 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:18]([C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)P(OC1C=CC=CC=1)(=O)OC1C=CC=CC=1.CC(C)([O-])C.[K+]>O1CCOCC1.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:10]#[C:18][C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 15142530Diphenyl [chloro(pyridin-4-yl)methyl]phosphonateHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 19707442HCID 19707442, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 3-cyclopentyloxy-4-methoxybenzaldehyde (6.07 g, 27.6 mmol) and diphenyl 1-chloro-1-(4-pyridyl)methanephosphonate (J. Org. Chem., 1992, 57, 1622) (9.03 g, 52.1 mmol) in dioxane (150 mL) there was added in portions potassium tert-butoxide (7.03 g, 62.8 mmol). The mixture was stirred at room temperature for 1 h and then refluxed. After 3.5 h, there was added another 7 g of potassium tert-butoxide and refluxing was continued for 18 h. After cooling, the mixture was diluted with water (1 L) and extracted 3 times with EtOAc. The extracts were washed 3 times with water, dried and evaporated and the residue was chromatographed on silica gel (EtOAc/hexane 1:2) to afford the title acetylene (4.72 g, 64%) as a cream-colored solid.

Workup

  1. temperaturerefluxed
  2. waitAfter 3.5 h
  3. temperaturerefluxing
  4. waitwas continued for 18 h
  5. temperatureAfter cooling
  6. extractionextracted 3 times with EtOAc
  7. washThe extracts were washed 3 times with water
  8. customdried
  9. customevaporated
  10. customthe residue was chromatographed on silica gel (EtOAc/hexane 1:2)

Sources & evidence

ORD record
ord-1e681435872a47d883ec45472cb3ccb0
Source dataset
uspto-grants-1998_01
Patent number
US05710170

Reaction notes

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