Sodium Bicarbonate → HCID 131719145, compound

HRID 2210281Notes

Reaction equation

HRID 2210281 reaction equation
[O:1]([C@H:19]1[CH2:53][C@H:52]([O:54][C:55]([O:57][CH3:58])=[O:56])[C@@:51]2([CH3:59])[C:21](=[CH:22][CH:23]=[C:24]3[C@@H:50]2[CH2:49][CH2:48][C@@:47]2([CH3:60])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[C@H:29]([CH3:46])[CH:30]=[CH:31][C@@H:32]2[CH2:36][CH2:35][CH2:34][C:33]2([O:38][Si](CC)(CC)CC)[CH3:37])[CH2:20]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:58][O:57][C:55]([O:54][C@@H:52]1[C@@:51]2([CH3:59])[C:21](=[CH:22][CH:23]=[C:24]3[C@@H:50]2[CH2:49][CH2:48][C@@:47]2([CH3:60])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[C@H:29]([CH3:46])[CH:30]=[CH:31][C@@H:32]2[CH2:36][CH2:35][CH2:34][C:33]2([OH:38])[CH3:37])[CH2:20][C@@H:19]([OH:1])[CH2:53]1)=[O:56]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium Fluoride2×HCID 131719146HCID 131719146, compound

Product 1

HCID 131719145HCID 131719145, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 13a (719 mg, 0.845 mmol) in THF (15 mL) was added a solution of tetra-n-butylammonium fluoride (1.0M in THF, 2.5 mL), and the mixture was stirred at ambient temperature for 1.5 h. A solution of tetra-n-butylammonium fluoride (1.0M in THF, 2.5 mL) was added twice to the mixture, and the mixture was stirred at ambient temperature overnight. The mixture was poured into cold NaHCO3 solution, and the mixture was extracted with EtOAc. The combined organic layers were washed with NaCl solution, and dried over Na2SO4. Filtration and concentration gave 0.97 g of a crude product, which was purified by column chromatography (SiO2 gel 30 g, EtOAc in n-hexane 20-50%), to give 373 mg (88.5%) of 14a, as white solids.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and concentration
  6. customgave 0.97 g of a crude product, which
  7. customwas purified by column chromatography (SiO2 gel 30 g, EtOAc in n-hexane 20-50%)

Sources & evidence

ORD record
ord-e762af6969f445698939f477e7dcda96
Source dataset
uspto-grants-1995_10
Patent number
US05457217

Reaction notes

Loading…