Triacetoxyperiodinane → HCID 62653892, compound

HRID 2406438Notes

Reaction equation

HRID 2406438 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:13](=[O:15])[CH3:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 62651773HCID 62651773, compound

Product 1

HCID 62653892HCID 62653892, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-(4-fluorophenyl)thiazol-5-yl)ethanol (1.0 g, 4.4 mmol) in dichloromethane (40 mL) was cooled to 0° C. Dess-Martin periodinane (5.7 g, 13.4 mmol) was added slowly at 0° C. and the reaction mixture stirred at room temperature for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution (80 mL), sodium thiosulfate solution (20 mL), extracted with ether (2×1000 mL), the organic layer dried over Na2SO4, filtered and concentrated to obtain crude product. The crude product was purified by Combiflash® chromatography (40% ethyl acetate in hexane) to afford 1-(2-(4-fluorophenyl)thiazol-5-yl)ethanone as off-white solid (820 mg, 83% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.67 (s, 1H), 8.08 (t, 2H), 7.37 (t, 2H), 2.59 (s, 3H); LC-MS m/z calculated for [M+H]+ 222.03, found 222.3.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution (80 mL), sodium thiosulfate solution (20 mL)
  2. extractionextracted with ether (2×1000 mL)
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto obtain crude product
  7. customThe crude product was purified by Combiflash® chromatography (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-73d532aa6d664a3284a3066267d82195
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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