Water → HCID 59527005, compound

HRID 384454Notes

Reaction equation

HRID 384454 reaction equation
[CH:1]1([O:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.O>CS(C)=O.ClCCl.C(N(CC)CC)C>[CH:1]1([O:4][CH2:5][CH2:6][CH2:7][CH:8]=[O:9])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 962WaterHCID 538523571135034-80-8

Product 1

HCID 59527005HCID 59527005, compoundYield 59.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-(cyclopropyloxy)butan-1-ol (400 mg) was dissolved in a mixture of DMSO (3.5 mL), dichloromethane (10 mL), and triethylamine (2.14 mL), and a solution of a sulfur trioxide pyridine complex (1.47 g) in DMSO (3.5 mL) added dropwise thereto under ice-cooling. The reaction mixture was stirred under ice-cooling for 1 hour, and then poured into water (20 mL). The mixture was extracted with diethyl ether (200 mL), the organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20) to obtain 4-(cyclopropyloxy)butanal (233 mg).

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 1 hour
  3. extractionThe mixture was extracted with diethyl ether (200 mL)
  4. washthe organic layer was washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-04b3893818624f2e8d99633ae25ccd74
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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