Dimethyl Sulfoxide → (1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehyde

HRID 901061Notes

Reaction equation

HRID 901061 reaction equation
[CH2:1]([C:3]1([CH2:18][CH2:19][OH:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].C(Cl)Cl.CS(C)=O.N1C=CC=CC=1.S(=O)(=O)=O>O>[CH2:1]([C:3]1([CH2:18][CH:19]=[O:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 168533Sulfur trioxide-pyridineHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

Product 1

HCID 20516149(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of compound 1 (136 mg, 0.5 mmol), CH2Cl2 (2 mL), dry DMSO (142 μL, 2.0 mmol, 4.0 eq), and dry TEA (697 μL, 5.0 mmol, 10.0 eq) at room temperature under argon, sulfur trioxide-pyridine complex (Pyr-SO3, 318 mg, 2.0 mmol, 4.0 eq) was added in a portion-wise manner and stirred for two days. The resulting mixture was then diluted with water and extracted three times with Et2O. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 20:80:EtOAc:Hexane to give a yellow-white solid (70 mg, 52%). Spectral data were identical to those reported above.

Workup

  1. extractionextracted three times with Et2O
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-c3fb4fe9b23546a59fd17778c8b98e28
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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