Hydrochloric Acid → HCID 14718764, compound

HRID 1088319Notes

Reaction equation

HRID 1088319 reaction equation
CO[CH2:3][C:4]1[C:13]([F:14])=[C:12](F)[C:7]([C:8](OC)=[O:9])=[C:6]([S:16][CH3:17])[C:5]=1[F:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[F:18][C:5]1[C:6]([S:16][CH3:17])=[C:7]([CH:12]=[C:13]([F:14])[C:4]=1[CH3:3])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14718887HCID 14718887, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14718764HCID 14718764, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 4-(methoxymethyl)-2-methylthio-3,5,6-trifluorobenzoate (0.48 g) was dissolved in dry tetrahydrofuran (2 cm3) under a nitrogen atmosphere at room temperature. To the stirred solution was added dropwise a solution of lithium aluminum hydride (1.0 cm3 of a 1.0 molar solution in THF). The mixture was stirred for 0.5 hour then stored for 18 hours. The solution was treated with 2 molar hydrochloric acid and extracted with dichloromethane (twice), dried (anhydrous magnesium sulphate), and evaporated under reduced pressure to give a pale yellow liquid (0.37 g). The liquid was fractionated by eluting through a bed of silica gel with dichloromethane/ethyl acetate (50:1 by volume) to yield the title product (0.04 g).

Workup

  1. waitthen stored for 18 hours
  2. extractionextracted with dichloromethane (twice),
  3. dry with materialdried (anhydrous magnesium sulphate)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1e8e55220264403681e750dcc2b00c6d
Source dataset
uspto-grants-1990_10
Patent number
US04962109

Reaction notes

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