Water → 8-(Trifluoromethoxy)chroman-4-one

HRID 536452Notes

Reaction equation

HRID 536452 reaction equation
Cl[C:2]#[C:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]([F:16])([F:15])[F:14].[OH2:17]>C(O)CO>[F:14][C:13]([F:16])([F:15])[O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[O:5][CH2:4][CH2:3][C:2]2=[O:17]

Participants

4

Reactant 2

HCID 962WaterHCID 685950081-(3-Chloroprop-2-ynyloxy)-2-(trifluoromethoxy)benzene

Product 1

HCID 227083508-(Trifluoromethoxy)chroman-4-oneYield 28%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of the product of Example 6B (12.8 g, 51.2 mmol) in ethylene glycol (200 mL) was heated at reflux for 6 hours, cooled to ambient temperature, stirred for 16 hours at ambient temperature, then heated at reflux for an additional 3 hours. After cooling, the reaction mixture was poured into water (100 mL) and extracted with diethyl ether (250 mL). The mixture was partitioned and the organic portion was concentrated. The resulting residue was purified by silica gel chromatography (gradient elution, 0%-20% EtOAc/hexanes) to obtain the title compound (3.62 g, 28% for three steps). 1H NMR (300 MHz, CDCl3) δ 7.86 (dd, J=8.1, 1.7 Hz, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.05-6.98 (m, 1H), 4.66-4.60 (m, 2H), 2.90-2.84 (m, 2H).

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureheated
  3. temperatureat reflux for an additional 3 hours
  4. temperatureAfter cooling
  5. extractionextracted with diethyl ether (250 mL)
  6. customThe mixture was partitioned
  7. concentrationthe organic portion was concentrated
  8. customThe resulting residue was purified by silica gel chromatography (gradient elution, 0%-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-54409972c6354df19ffe29c82a0e2f6d
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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