HCID 89524950, compound → HCID 117599366, compound

HRID 1466159Notes

Reaction equation

HRID 1466159 reaction equation
[F:1][CH:2]([C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[CH:8]=1)[CH:3]([OH:6])CO.C(Cl)(Cl)(Cl)Cl.O.CC(O)(C)C>C(Cl)(Cl)(Cl)Cl.CC(O)(C)C.O>[F:1][CH:2]([C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[CH:8]=1)[CH:3]=[O:6]

Participants

5

Reactant 2

HCID 89524950HCID 89524950, compoundHCID 131732688HCID 131732688, compound

Product 1

HCID 117599366HCID 117599366, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 86612767HCID 86612767, compoundSolvent

Procedure

NaIO4 (71 mg, 0.33 mmol) was added to a stirring solution of 5-(1-Fluoro-2,3-dihydroxypropyl)-2-benzofuran-1(3H)-one (30 mg, 0.13 mmol) in 5:2:2 CCl4-H2O-t-BuOH (5 mL) (the starting material was dissolved in CCl4-t-BuOH, and H2O was added last). After stirring 1.5 hours, the suspension was diluted with H2O (3 mL) and extracted with CH2Cl2 (50 mL). The combined organic extracts were washed with 10% aqueous NaHSO3 (8 mL) and water (8 mL), dried over Na2SO4 and evaporated. The residue was purified by prep-TLC to give the title product

Workup

  1. extractionextracted with CH2Cl2 (50 mL)
  2. washThe combined organic extracts were washed with 10% aqueous NaHSO3 (8 mL) and water (8 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-fa19ac5f96db47dc9d7a2618090d435c
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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