Sulfuric Acid → HCID 22012183, compound

HRID 378552Notes

Reaction equation

HRID 378552 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-tert-butyl aluminium hydride (120 ml of an 1 M solution in toluene) was added dropwise at -10° C. followed by stirring for 2 h at room temperature. Dilute sulfuric acid (2 M, 300 ml) was added, the phases separated, the aqeous 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 aqeous 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-20e08e865e094b6ca8a8acd7a38b0e3a
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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