Lithium tri-tert-butoxyaluminohydride → HCID 20271506, compound

HRID 485106Notes

Reaction equation

HRID 485106 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:14])(=[O:13])[C:11]3[CH:15]=[C:16]([C:19](Cl)=[O:20])[CH:17]=[CH:18][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:22]=1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C(COC)OC>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:14])(=[O:13])[C:11]3[CH:15]=[C:16]([CH:19]=[O:20])[CH:17]=[CH:18][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:22]=1

Participants

4

Reactant 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 54178625HCID 54178625, compound

Product 1

HCID 20271506HCID 20271506, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Dissolve the crude 8-methylthiodibenzo[b,f]thiepin-3-carboxylic acid chloride-5,5-dioxide in glyme, and with stirring under dry nitrogen, add a filtered solution of 1.1 equivalents of lithium tri-tertiary butoxy-aluminum hydride in glyme dropwise with cooling (ice-bath). Stir the mixture for 1 hour after the addition is complete and pour into ice-cold dilute hydrochloric acid. Isolate the crude title compound by extraction with chloroform and purify the compound by column chromatography on silica gel usin toluene as the solvent.

Workup

  1. temperaturewith cooling (ice-bath)
  2. stirringStir the mixture for 1 hour
  3. additionafter the addition
  4. additionpour into ice-cold dilute hydrochloric acid

Sources & evidence

ORD record
ord-7088794ceeff40e882fba38305b674a5
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

Loading…