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

HRID 1265625Notes

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](CO)[S:13][C:14]=2[CH3:15])[CH:5]=1.[O:19]1[CH:24]=CCCC1.[OH2:25].[C:26]1(C)C=[CH:30][C:29](S(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([CH2:24][O:19][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][O:25]3)[CH:14]([CH3:15])[S:13][CH:12]=[N:11]2)[CH:5]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 3-(2-hydroxymethyl-5-methyl-thiazol-4-yl)-benzoic acid methyl ester (1.05 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 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-[5-methyl-4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-benzoic acid methyl ester (1.45 g) as a pale-yellow oil.

Workup

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

Sources & evidence

ORD record: ord-db380c7ca37c4bee87c8cecd94f28515
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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