Methane → HCID 58720312, compound

HRID 1787527Notes

Reaction equation

HRID 1787527 reaction equation
CC(C)([O-])C.[K+].O[C@@:8]([CH3:37])([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:33]3[S:34][CH:35]=[CH:36][C:32]=3[O:31][N:30]=2)[CH:24]=1)[CH2:9][O:10]S(C1C=CC(C)=CC=1)(=O)=O.C>O1CCCC1>[CH3:37][C@:8]1([CH2:21][O:22][C:23]2[CH:24]=[C:25]([C:29]3[C:33]4[S:34][CH:35]=[CH:36][C:32]=4[O:31][N:30]=3)[CH:26]=[CH:27][CH:28]=2)[CH2:9][O:10]1

Participants

5

Reactant 3

HCID 297MethaneHCID 9825448HCID 9825448, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58720312HCID 58720312, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add potassium t-butoxide (0.67 g, 0.006 mol) in small portions to a chilled (0° C.) stirred solution of toluene-4-sulfonic acid (S)-2-hydroxy-2-methyl-3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl ester (2.45 g, 0.00533 mol) and tetrahydrofuran (40 mL). Stir one hour at 0° C. and partition between ethyl acetate and water. Separate the organic phase, dry (MgSO4), filter, and concentrate in vacuo. Recrystallize the residue from ether-hexane to give the title compound (1.33 g, 87% yield), m.p. 84-85° C., MS (chemical ionization, CH4) MH+ 288.

Workup

  1. custompartition between ethyl acetate and water
  2. customSeparate the organic phase
  3. dry with materialdry (MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customRecrystallize the residue from ether-hexane

Sources & evidence

ORD record
ord-447030c0390442bfbeac224020bf1117
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

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