Sodium Bicarbonate → HCID 68742660, compound

HRID 2378535Notes

Reaction equation

HRID 2378535 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([O:16][CH3:17])[C:7]=1[O:8][Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([O:16][CH3:17])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68743981HCID 68743981, compound

Product 1

HCID 68742660HCID 68742660, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Intermediate 18 (750 mg) in THF (50 ml) was added with a 1 M solution of tetrabutylammonium fluoride in THF (5 ml, TCI), and stirred for 1.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (30 ml), and extracted with ethyl acetate (50 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate 19, 542 mg).

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2ed945e264fd494f8ede6b29f30d8cce
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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