Benzothiazole → 1,3-Benzothiazol-2-yl[5-(dimethoxymethyl)-2-fluorophenyl]methanol

HRID 503109Notes

Reaction equation

HRID 503109 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[CH3:15][O:16][CH:17]([O:27][CH3:28])[C:18]1[CH:19]=[CH:20][C:21]([F:26])=[C:22]([CH:25]=1)[CH:23]=[O:24].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:23]([C:22]1[CH:25]=[C:18]([CH:17]([O:16][CH3:15])[O:27][CH3:28])[CH:19]=[CH:20][C:21]=1[F:26])[OH:24]

Participants

7

Reactant 4

HCID 7222BenzothiazoleHCID 25517Ammonium ChlorideHCID 222607045-(Dimethoxymethyl)-2-fluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 222608481,3-Benzothiazol-2-yl[5-(dimethoxymethyl)-2-fluorophenyl]methanolYield 79.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A total of 1.08 g of benzothiazole was dissolved in 15 ml of dry tetrahydrofuran. After cooling to −78° C. in an atmosphere of nitrogen gas, 6.4 ml of 1.56 M solution of n-butyllithium in hexane was added. After stirring for 5 minutes, 8 ml of a solution of 1.35 g of 5-(dimethoxymethyl)-2-fluorobenzaldehyde in dry tetrahydrofuran was added, followed by stirring for 10 minutes. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate for two times. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=3:7), to give 1.8 g of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. stirringby stirring for 10 minutes
  3. extractionthe mixture was extracted with ethyl acetate for two times
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-7c17faf0ce1a40208dd88888a9a8673b
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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