Sodium hydride → Ethyl 2-(4-chloro-1-hydroxy-6-(methylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate
Reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1.[H-].[Na+].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CN(C=O)C>[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][S:22]([CH3:21])(=[O:24])=[O:23])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (60 mg, 0.22 mmol) in DMF (3 mL) was slowly added NaH (27 mg, 0.66 mmol) at 0° C. The reaction mixture was stirred for 20 min and MsCl (29 mg, 0.27 mmol) was added. The reaction mixture was stirred overnight at room temperature and quenched with ice water. The resulting mixture was extracted with EtOAc (2×15 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was used directly in the next step reaction without further purification. MS (ESI) m/z=349 [M+H]+.
Workup
- customat 0° C
- stirringThe reaction mixture was stirred overnight at room temperature
- customquenched with ice water
- extractionThe resulting mixture was extracted with EtOAc (2×15 mL)
- dry with materialthe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was used directly in the next step reaction without further purification
Sources & evidence
- ORD record
- ord-7b5652e8e0874762b4de2522b3a22e48
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343944B2
Reaction notes
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