Ethyl formate → HCID 70373861, compound

HRID 2352449Notes

Reaction equation

HRID 2352449 reaction equation
[CH:1](OCC)=[O:2].[CH3:6][C:7]([CH3:23])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)[C:8](=[O:10])[CH3:9].C[O-].[Na+]>C(OCC)C>[CH3:6][C:7]([CH3:23])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:19]([F:21])([F:22])[F:20])=[CH:14][CH:13]=1)[C:8](=[O:10])[CH:9]=[CH:1][OH:2]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 14304257HCID 14304257, compound

Product 1

HCID 70373861HCID 70373861, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

34.7 g (0.469 mole) of ethyl formate are added dropwise with stirring to 129.4 g (0.469 mole) of 3,3-dimethyl-4-(4-trifluoromethylthiophenyl)-butan-2-one and 25.3 g (0.469 mole) of sodium methylate in 1 liter of diethyl ether at room temperature, and the mixture is stirred at room temperature for 4 hours after the addition is complete. For work-up, the mixture is extracted with 1 liter of water, and the combined aqueous extracts are washed once with diethyl ether, acidified to pH 1-2 with dilute aqueous hydrochloric acid and extracted with dichloromethane. The dichloromethane phase is dried over sodium sulphate and concentrated in vacuo. 90.5 g of 4,4-dimethyl-5-(4-trifluoromethylthiophenyl)-penten-1-ol-3-one are obtained; these are dissolved in 200 ml of methanol and 17.0 g (0.315 mol) of sodium methylate are added. Concentrating the solution in vacuo gives 97.1 g (75% of theory) of the sodium salt of 4,4-dimethyl-5-(4-trifluoromethylthiophenyl)-1 -penten-1-ol-3-one as a resin, which is further reacted without purification. ##STR875##

Workup

  1. additionafter the addition
  2. extractionFor work-up, the mixture is extracted with 1 liter of water
  3. washthe combined aqueous extracts are washed once with diethyl ether
  4. extractionextracted with dichloromethane
  5. dry with materialThe dichloromethane phase is dried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48e681581f024d59b485cfa2fec1179e
Source dataset
uspto-grants-1989_10
Patent number
US04877446

Reaction notes

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