Tetrahydrofuran → HCID 86209430, compound

HRID 606339Notes

Reaction equation

HRID 606339 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH:10]=[CH:11][C:12]=1[CH:13]=O)[CH:4]=[CH2:5].[CH2:23]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH:10]=[CH:11][C:12]=1[CH:13]=[CH2:23])[CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 86209429HCID 86209429, compound

Product 1

HCID 86209430HCID 86209430, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8058HexaneSolvent

Procedure

Methyltriphenylphosphonium bromide (1.95 g, 5.45 mmol) was added to a suspension of sodium hydride (60% in oil) (0.25 g, 6.3 mmol) in THF (35 ml) at 0 C. and it was stirred for 30 min at room temperature. To the above solution was added solution of trifluoro-methanesulfonic acid 3-allyloxy-4-formyl-phenyl ester (1.3 g, 4.2 mmol) in THF (15 ml), and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with hexane and extracted with water. Organic phase was washed with brine and evaporated. Silica gel column chromatography (EA:Hex, 1:20) afforded trifluoro-methanesulfonic acid 3-allyloxy-4-vinyl-phenyl ester (0.68 g, 53%).

Workup

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. extractionextracted with water
  3. washOrganic phase was washed with brine
  4. customevaporated

Sources & evidence

ORD record
ord-a91fde169901442ebcf1b596c473258e
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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