Triacetoxyperiodinane → HCID 18185015, compound

HRID 1993879Notes

Reaction equation

HRID 1993879 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][OH:13])[CH2:6]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH:12]=[O:13])[CH2:6]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 668775125-Trifluoromethyl-indan-2-yl-methanol

Product 1

HCID 18185015HCID 18185015, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above 5-trifluoromethyl-indan-2-yl-methanol (216 mg, 1 mmol) was dissolved in methylene chloride (15 mL) and the solution was cooled in an ice bath. To this solution was added Dess-Martin reagent (450 mg, 1.06 mmol) in four portions. The mixture was warmed to room temperature and stirred for 1 hr. The mixture was evaporated to dryness and the residue was triturated with petroleum ether (14 mL) and ether (7 mL). The precipitate was filtered out and the filtrate was extracted with ether and sodium bicarbonate solution. The organic layer was dried over sodium sulfate and solvents were evaporated to give 5-trifluoromethyl-indan-2-carbaldehyde (210 mg) as pale green oil. 1H-NMR (CDCl3) □ 9.78 (s, 1H), 7.48 (s, 1H), 7.43 (d, 1H), 7.32 (d, 1H), 3.33-3.38 (m, 3H), 3.15-3.27 (m, 2H).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customThe mixture was evaporated to dryness
  3. customthe residue was triturated with petroleum ether (14 mL) and ether (7 mL)
  4. filtrationThe precipitate was filtered out
  5. extractionthe filtrate was extracted with ether and sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over sodium sulfate and solvents
  7. customwere evaporated

Sources & evidence

ORD record
ord-c025d9911ba5488c975d39755884a3b3
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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