Triethylamine → Methyl 4-formylcyclohexane-1-carboxylate

HRID 2170772Notes

Reaction equation

HRID 2170772 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.S(=O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 178501147HCID 178501147, compound

Product 1

HCID 11252253Methyl 4-formylcyclohexane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

The title intermediate (700 mg, 1.87 mmol, 40%) was obtained as a white solid from 4-formyl-cyclohexanecarboxylic acid methyl ester (800 mg, 4.7 mmol) and 4-iodoaniline (601 mg, 2.74 mmol) analogously to Intermediate 75.7. HPLC: GtRet=7.874 min; LC-MS: m/z 374.2 [M+H]+. 4-Formyl-cyclohexanecarboxylic acid methyl ester was prepared by the following method. To a solution of trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (which is reported in Synthesis Comm. (1982) page 42-43) (861 mg, 5.0 mmol) and Et3N (2.1 mL, 15.0 mmol) in DCM (16 mL) was slowly added a solution of pyridine sulfur trioxide (2.39 g, 15 mmol) in DMSO (10 mL) at 0° C. (ice bath). After 70 min stirring, it was then diluted into DCM and washed with water. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. This crude material (0.8 g, 4.7 mmol) was used for the next step without further purification.

Workup

  1. customGtRet=7.874 min
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fb79e48e097f4750b8dff6e1b8ef3114
Source dataset
uspto-grants-2015_06
Patent number
US09051279B2

Reaction notes

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