Tetrahydrofuran → HCID 68510882, compound

HRID 1715054Notes

Reaction equation

HRID 1715054 reaction equation
CC(C)([O-:4])C.[K+].[F:7][C:8]1[CH:9]=[C:10]([S:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23]([CH:27]=O)=[CH:22][CH:21]=[CH:20]3)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>>[CH2:33]([O:32][C:31](=[O:4])[CH:30]=[CH:27][C:23]1[C:24]2[C:19](=[CH:18][C:17]([S:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([F:7])[CH:9]=3)(=[O:16])=[O:15])=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1)[CH3:29]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 59028774HCID 59028774, compound

Product 1

HCID 68510882HCID 68510882, compound

Procedure

Potassium tert-butoxide (6.5 mL of 1M THF solution) was added dropwise to 1.3 mL of triethylphosphonyl acetate (6.5 mmol) at 0° C. This solution was then added dropwise to a room temperature solution of 6-(3-Fluoro-benzenesulfonyl)-naphthalene-1-carbaldehyde (1.7 g, 5.4 mmol) in 100 mL THF. The reaction mixture was stirred for 18 hours at room temperature, then quenched with dilute aqueous HCl. The mixture was extracted with EtOAc, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give 2.1 g of crude 3-[6-(3-fluoro-benzenesulfonyl)-naphthalen-1-yl]-acrylic acid ethyl ester, which was used directly without further purification.

Workup

  1. customquenched with dilute aqueous HCl
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ea6b4dc10a3404b867196cb85ce68be
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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