Hydrochloric Acid → HCID 58292803, compound

HRID 1798109Notes

Reaction equation

HRID 1798109 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([F:16])[C:7]1=2)[CH3:2].[H-].[Na+].I[CH:22]([CH3:24])[CH3:23].Cl>CN(C=O)C>[F:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:17][CH:22]([CH3:24])[CH3:23])[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 58292615HCID 58292615, compound

Product 1

HCID 58292803HCID 58292803, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl-2-(4-fluoro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.254 g, 1.0 mmol) in DMF (4 mL) was added sodium hydride (0.12 g, 3.0 mmol). The reaction mixture was stirred for 30 min and then 2-iodopropane (0.19 g, 1.1 mmol) was added. After stirring for an additional 2 h, the reaction mixture was acidified to pH=2 using diluted hydrochloride acid and extracted with ethyl acetate (15 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give the crude product as a yellow solid (0.25 g, Yield: 84%) which was used immediately without further purification. MS (ESI) m/z=297 [M+H]+.

Workup

  1. stirringAfter stirring for an additional 2 h
  2. extractionextracted with ethyl acetate (15 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f61be0606d3b4f9d8debbc21c50dd489
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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