3,4-dihydro-2H-pyran → 3-[5-Propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-benzoic acid methyl ester

HRID 1265628Notes

Reaction equation

HRID 1265628 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([CH2:16][OH:17])SC=2C)[CH:5]=1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.[C:26]1(C)C=C[C:29]([S:32](O)(=O)=O)=[CH:28][CH:27]=1>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:32][C:29]([CH2:28][CH2:27][CH3:26])=[C:12]([CH2:16][O:17][CH:24]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[N:11]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 18548740Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate

Product 1

HCID 696888463-[5-Propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-(2-hydroxymethyl-5-methyl-thiazol-4-yl)-benzoic acid methyl ester (0.38 g), dihydropyrane (0.73 mL) and p-toluenesulfonic acid hydrate (0.07 g) in AcOEt (10 mL) was stirred at 20° C. for 1 h. The solution was diluted with AcOEt, washed with 5% NaHCO3 solution and brine, dried and evaporated. The residual oil was purified by chromatography on silica gel using AcOEt/hexane (1:3) as eluent to give 3-[5-propyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-benzoic acid methyl ester (0.36 g) as a pale-yellow oil.

Workup

  1. washwashed with 5% NaHCO3 solution and brine
  2. customdried
  3. customevaporated
  4. customThe residual oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cd94beec40514347a534c850a62724fa
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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