Sulfuric Acid → 3-Trifluoromethyl-2-penten-1-ol

HRID 888340Notes

Reaction equation

HRID 888340 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([CH2:10][CH3:11])=[CH:4][C:5](OCC)=[O:6].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)O>O1CCCC1>[F:1][C:2]([F:13])([F:12])[C:3]([CH2:10][CH3:11])=[CH:4][CH2:5][OH:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 76705621Ethyl 3-trifluoromethyl-2-pentenoate

Product 1

HCID 866429883-Trifluoromethyl-2-penten-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 g of a mixture of (E) and (Z) isomers of ethyl 3-trifluoromethyl-2-pentenoate in 100 ml of tetrahydrofuran was added dropwise 100 ml of diisobutylaluminum hydride (1.02M solution in hexane) under ice-cooling, and then stirred at the same temperature for 2 hours. To the reaction mixture was added diluted sulfuric acid and then extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain crude 3-trifluoromethyl-2-penten-1-ol as a mixture of (E) and (Z) isomers.

Workup

  1. temperaturecooling
  2. extractionextracted with t-butyl methyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b891576aaf3f4223ac59ec07f24d5bdb
Source dataset
uspto-grants-2012_08
Patent number
US08247595B2

Reaction notes

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