Methanol → HCID 69418093, compound

HRID 1375087Notes

Reaction equation

HRID 1375087 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][C:15]([OH:17])=[O:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:18]O>S(=O)(=O)(O)O>[CH3:18][O:16][C:15](=[O:17])[CH2:14][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 21077947HCID 21077947, compound

Product 1

HCID 69418093HCID 69418093, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A stirred solution of (4-{4-chloro-phenyl}-tetrahydro-pyran-4-yl)-acetic acid [3.3 g, Reference Example 21(a)] in anhydrous methanol (125 mL), under argon, was treated with concentrated sulfuric acid (8 drops). This mixture was stirred at reflux temperature for 5.5 hours then evaporated. The residue was treated with ethyl acetate (35 mL) and the resulting solution was washed three times with water (10 mL), then dried over magnesium sulfate and then evaporated to give the title compound (3.12 g) as a pale amber oil. LC-MS: RT=3.43 minutes, MS(ES+): 269 and 271(M+H)+.

Workup

  1. temperatureat reflux temperature for 5.5 hours
  2. customthen evaporated
  3. additionThe residue was treated with ethyl acetate (35 mL)
  4. washthe resulting solution was washed three times with water (10 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-006855bb233c4a5bbfac880e371c0697
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

Loading…