HCID 21883512, compound → HCID 21883572, compound

HRID 722387Notes

Reaction equation

HRID 722387 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:19]([F:22])([F:21])[F:20])[O:8][C:9]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=2[C:11]=1[CH:12]=[CH2:13])=[O:5])[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:19]([F:20])([F:22])[F:21])[O:8][C:9]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=2[C:11]=1[CH2:12][CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 21883512HCID 21883512, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21883572HCID 21883572, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl-6-chloro-4-ethenyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylate (Example 142,Step 5)(0.433 g, 1.30 mmol) was dissolved in methanol (10 mL). Palladium(5 wt % on activated carbon)(0.150 g) was slowly added. The reaction vessel was charged with hydrogen (25 psi) and was stirred for 25 minutes. Gas chromatographic analysis indicated that the reaction was complete. The reaction mixture was filtered through Celite and evaporated to yield a orange oil. The oil was purified by flash column chromatography(100 % hexanes) to yield the desired product as a yellow oil (0.282 g, 65%): 1H NMR (CDCl3/300 MHz) 7.43 (d, 1H, J=2.4 Hz), 7.25 (dd, 1H, J=2.4, 8.7 Hz), 6.92(d, 1H, J=8.7 Hz), 5.75 (q, 1H, J=7.0 Hz), 4.38–4.24 (m, 2H), 3.05–2.95 (m, 2H), 1.35 (t, 3H, J=7.2 Hz), 1.25, (t, 3H, J=7.6 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated
  3. customto yield a orange oil
  4. customThe oil was purified by flash column chromatography(100 % hexanes)

Sources & evidence

ORD record
ord-1f14b6f3074143a19ef51298d1702e32
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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