Benzothiazole → HCID 22408313, compound

HRID 439833Notes

Reaction equation

HRID 439833 reaction equation
C([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[CH:15](=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18]>C1COCC1>[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH:15]([OH:20])[CH2:16][CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 7222BenzothiazoleHCID 115523-MethylbutanalHCID 178418339Butyllithium

Product 1

HCID 22408313HCID 22408313, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyllithium (2.5M in hexanes; 65.1 ml, 0.163 mol) was added to a stirred solution of benzothiazole (20.0 g, 0.148 mol) in dry THF (250 ml) under argon at -78° C. After 10 min a solution of isovaleraldehyde (17.4 ml, 0.163 mol) in dry THF (50 ml) was added slowly and the mixture stirred for 1 h at -78° C. The reaction mixture was removed from the cooling bath and after 10 min was quenched by the addition of excess water and the mixture extracted with ethyl acetate. The combined organic layers were washed with water, dried, filtered and evaporated. Chromatography (20-30% diethyl ether in hexane) gave 1-(2-benzothiazolyl)-3-methylbutanol (5.8 g, 18%) as an amorphous yellow solid.

Workup

  1. customThe reaction mixture was removed from the cooling bath and after 10 min
  2. customwas quenched by the addition of excess water
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eb766bb3b7b94866b7531316bf807908
Source dataset
uspto-grants-1996_05
Patent number
US05516783

Reaction notes

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