Water → (2-Methyl-5-m-tolylthiazol-4-yl)methanol

HRID 41590Notes

Reaction equation

HRID 41590 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[S:9][C:10]([C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[C:11]([C:13](OC)=[O:14])[N:12]=1.O>C1COCC1>[CH3:7][C:8]1[S:9][C:10]([C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[C:11]([CH2:13][OH:14])[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 532711842-Methyl-5-m-tolyl-thiazole-4-carboxylic acid methyl ester

Product 1

HCID 67251279(2-Methyl-5-m-tolylthiazol-4-yl)methanolYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of lithium aluminiumhydride (139 mg, 3.64 mmol) in THF (5 mL) a solution of methyl 2-methyl-5-m-tolylthiazole-4-carboxylate [1007873-98-4] (600 mg, 2.43 mmol) in THF (5 mL) was added at −25° C. and stirred for 30 min. Then water (5 mL) was added dropwise and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (eluent: 50% ethyl acetate in hexane) to yield the title compound (300 mg, 56%). [LCMS RtF=0.32 min, [M+H]+=219.9; TLC Rf=0.20 (methanol/chloroform 10:90)].

Workup

  1. additionwas added at −25° C.
  2. extractionthe mixture was extracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (eluent: 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d5b3a6aa37974f53b741d2321394a7a2
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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