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

HRID 1265632Notes

Reaction equation

HRID 1265632 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]([CH3:17])[S:13][C:14]=2[CH2:15][OH:16])[CH:5]=1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=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[N:11]=[C:12]([CH3:17])[S:13][C:14]=2[CH2:15][O:16][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][O:19]2)[CH:5]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 696880433-(5-Hydroxymethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester

Product 1

HCID 696890913-[2-Methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-(5-Hydroxymethyl-2-methyl-thiazol-4-yl)-benzoic acid methyl ester (0.38 g), dihydropyrane (2.01 mL) and p-toluenesulfonic acid hydrate (0.21 g) in AcOEt (25 mL) was stirred at 20° C. for 1 h. The solution was diluted AcOEt, washed with 5% NaHCO3 solution and with brine, dried and evaporated. The residual oil was purified by chromatography on silica gel using AcOEt/hexane (1:3) as eluent to give 3-[2-methyl-5-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl ester (3.8 g) as a pale-yellow oil.

Workup

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

Sources & evidence

ORD record
ord-6e01547c5cc345b19d4e6e882541a4aa
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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