Sulfuric Acid → HCID 22012183, compound

HRID 2393479Notes

Reaction equation

HRID 2393479 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, is 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-21a229f97ac448e3b23e428becb248fa
Source dataset
uspto-grants-1998_09
Patent number
US05807871

Reaction notes

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