Trifluoroacetic acid → 4-Isopropoxy-3-methylbenzaldehyde

HRID 1478443Notes

Reaction equation

HRID 1478443 reaction equation
C(O[C@H]1C[C@@H](C2C=CC=CN=2)OC2(CCNCC2)C1)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH:35]([O:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][C:40]=1[CH3:48])([CH3:37])[CH3:36]>ClCCl.O>[CH:35]([O:38][C:39]1[CH:47]=[CH:46][C:42]([CH:43]=[O:44])=[CH:41][C:40]=1[CH3:48])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 874026094-Isopropoxy-3-methyl-benzoyl chlorideHCID 117772336cis-8-Ethoxy-10-(2-pyridyl)-11-oxa-3-azaspiro[5.5]undecane

Product 1

HCID 509982434-Isopropoxy-3-methylbenzaldehydeYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-8-ethoxy-10-(2-pyridyl)-11-oxa-3-azaspiro[5.5]undecane; 2,2,2-trifluoroacetic acid (42 mg, 0.11 mmol) in dichloromethane (1 mL) was added triethylamine (75 μL, 0.54 mmol). 4-isopropoxy-3-methyl-benzoyl chloride (46 mg, 0.21 mmol) (˜50% pure) was added. The mixture was stirred at rt for 15 min. Water was added. The aqueous layer was extracted with dichloromethane (2×). The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified by column chromatography (40-60% ethyl acetate-hex) to provide cis-8-ethoxy-10-(2-pyridyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (37 mg). ESI-MS m/z calc. 452.27, found 453.3 (M+1)+; Retention time: 1.38 minutes (3 min run).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (2×)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude material was purified by column chromatography (40-60% ethyl acetate-hex)

Sources & evidence

ORD record
ord-841ddbf32ab04171850c3cade79d0232
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

Loading…