Dichloromethane → HCID 69517042, compound

HRID 854924Notes

Reaction equation

HRID 854924 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]([F:17])([F:16])[F:15])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]2)(=O)[CH3:2].ClCCl.C([SiH](CC)CC)C>O>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]([F:15])([F:16])[F:17])[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]2)[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 69518724HCID 69518724, compound

Product 1

HCID 69517042HCID 69517042, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 mL single-neck round bottom flask was charged with ethyl 6-acetyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (1.465 g, 4.662 mmole), dichloromethane (4 mL), and triethyl silane (1.71 mL, 1.25 g, 10.72 mmole) and stirred at RT overnight. The crude reaction was poured into water and extracted several times with dichloromethane. The combined organics were washed with water, then with aqueous 10% sodium carbonate solution, dried over MgSO4, filtered and concentrated in vacuo to yield a colorless oil. This oil was purified by silica chromatography (9 hexane: 1 ethyl acetate) yielding the title compound as a clear, colorless oil (1.25 g, 89%): 1H NMR (acetone-d6/300 MHz) 7.84 (s, 1H), 7.30 (d, 1H, J=2.0 Hz), 7.26 (dd, 1H, J=8.3, 2.0 Hz), 6.93 (d, 1H, J=8.3 Hz), 5.79 (q, 1H, J=7.3 Hz), 4.37-4.24 (m, 2H), 2.60 (q, 2H, J=7.6 Hz), 1.32 (t, 3H, J=7.3 Hz), 1.20 (t, 3H, J=7.6 Hz). GCMS m/z 300 (M+).

Workup

  1. customThe crude reaction
  2. extractionextracted several times with dichloromethane
  3. washThe combined organics were washed with water
  4. dry with materialwith aqueous 10% sodium carbonate solution, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a colorless oil
  8. customThis oil was purified by silica chromatography (9 hexane: 1 ethyl acetate)

Sources & evidence

ORD record
ord-ad5f241791bb4d4abf50c885f916bc3b
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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