3,4-dihydro-2H-pyran → HCID 69688429, compound

HRID 1265608Notes

Reaction equation

HRID 1265608 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2O[C:12]([CH2:15][OH:16])=[N:13][N:14]=2)[CH:5]=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC([S:31](O)(=O)=O)=CC=1>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:31][C:12]([CH2:15][O:16][CH:23]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[N:13][N:14]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 69688420HCID 69688420, compound

Product 1

HCID 69688429HCID 69688429, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 3-(5-hydroxymethyl-[1,3,4]oxadiazol-2-yl)-benzoic acid methyl ester (9.8 g), dihydropyrane (7.7 mL) and p-toluenesulfonic acid hydrate (0.80 g) in AcOEt (100 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 (1:2) as eluent to give 3-[5-(tetrahydro-pyran-2-yloxymethyl)-[1,3,4]thiadiazol-2-yl]-benzoic acid methyl ester (12.6 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-318a1ba44d5945eeb011927c210dedca
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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