Methanesulfonic Acid → HCID 71110824, compound

HRID 576301Notes

Reaction equation

HRID 576301 reaction equation
[Br:1][C:2]1[C:3]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)=[CH:4][C:5]([C:11]2([OH:38])[C@H:16]([O:17][Si](C)(C)C)[C@@H:15]([O:22][Si](C)(C)C)[C@H:14]([O:27][Si](C)(C)C)[C@@H:13]([CH2:32][O:33][Si](C)(C)C)[O:12]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.[CH3:48]S(O)(=O)=O>C1COCC1>[Br:1][C:2]1[C:3]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)=[CH:4][C:5]([C:11]2([O:38][CH3:48])[C@H:16]([OH:17])[C@@H:15]([OH:22])[C@H:14]([OH:27])[C@@H:13]([CH2:32][OH:33])[O:12]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71110541HCID 71110541, compound

Product 1

HCID 71110824HCID 71110824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of crude alcohol 14 (2.03 g) in anhydrous THF (11.9 mL) were added CH3SO3H (0.6 N in MeOH, 7.0 mL, 4.18 mmol) at −78° C. under nitrogen atmosphere. The mixture was slowly warmed up to −40° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution (15 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the crude intermediate 15, which was used without further purification (0.94 g, 1.85 mmol, 80%). [M−OMe]+ 477.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution (15 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bac77af16269414ba70e433abfccdddd
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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