HCID 21883512, compound → HCID 21883544, compound

HRID 1421619Notes

Reaction equation

HRID 1421619 reaction equation
C([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])C.[H][H]>CO.[Pd]>[Cl:18][C:15]1[CH:16]=[CH:17][C:9]2[O:8][CH:7]([C:19]([F:21])([F:20])[F:22])[C:6]([C:4]([OH:5])=[O:3])=[C:11]([CH2:12][CH3:13])[C:10]=2[CH:14]=1

Participants

5

Reactant 2

HCID 21883512HCID 21883512, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21883544HCID 21883544, compoundYield 70.7%

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-ab7f68b961264ccfa8dd79d6c994b545
Source dataset
uspto-grants-2000_06
Patent number
US06077850

Reaction notes

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