Sulfuric Acid → HCID 22012183, compound

HRID 1377498Notes

Reaction equation

HRID 1377498 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][CH2:12][C:13](O)=[O:14])=[N:2]1.[H-].C([Al+]C(C)(C)C)(C)(C)C.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[N:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21981631HCID 21981631, compoundHCID 22012272HCID 22012272, compound

Product 1

HCID 22012183HCID 22012183, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

4-(1,2-Benzisothiazol-3-yl)butyric acid (C. Branca et al, Phytochemistry 14, 1975, 2545) (17 g) was dissolved in dry toluene (500 ml) and cooled to -10° C. Di-tertbutyl aluminium hydride (120 ml of an 1M solution in toluene) was added dropwise at -10° C. followed by stirring for 2 h at room temperature. Dilute sulfuric acid (2M, 300 ml) was added, the phases separated, the aqueous phase extracted with ether, and the combined organic phases dried over magnesium sulfate. Removal of solvents in vacuo left a viscous oil which was purified by column chromatography (silica gel, eluent:ether). 4-(1,2-Benzisothiazol-3-yl)-1-butanol (5.2 g) was obtained as an oil.

Workup

  1. customthe phases separated
  2. extractionthe aqueous phase extracted with ether
  3. dry with materialthe combined organic phases dried over magnesium sulfate
  4. customRemoval of solvents in vacuo
  5. waitleft a viscous oil which
  6. customwas purified by column chromatography (silica gel, eluent:ether)

Sources & evidence

ORD record
ord-22c8142fed11406a8790ee19882e6b98
Source dataset
uspto-grants-1997_09
Patent number
US05665725

Reaction notes

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