Sodium Bicarbonate → HCID 57696848, compound

HRID 217624Notes

Reaction equation

HRID 217624 reaction equation
[Si](OC(=C)[CH2:10][C@@:11]([C@@H:14]1[C@:22]2([CH3:23])[C@H:17]([C@@H:18]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15]1)([OH:13])[CH3:12])(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)[CH2:34][CH2:35][CH2:36]C.[F-].C([O-])(O)=[O:52].[Na+]>C1COCC1>[Si:25]([O:24][C@@H:18]1[C@H:17]2[C@@:22]([CH3:23])([C@@H:14]([C@:11]([OH:13])([CH3:12])[CH2:10][C:35](=[CH2:36])[CH2:34][OH:52])[CH2:15][CH2:16]2)[CH2:21][CH2:20][CH2:19]1)([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68947091HCID 68947091, compound

Product 1

HCID 57696848HCID 57696848, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7 (1.3 g, 2.6 mmol) in dry THF (6 mL) was treated with a nBu4NF (1.6 g, 5 mmol). After 1 h, a saturated solution of NaHCO3 (30 mL) was added. The mixture was extracted with EtOAc (3×30 mL). The organic phase was dried, filtered and concentrated in vacuum. The residue was purified by flash chromatography (SiO2, 3×10 cm, 25% Et2O-hexanes) to give 8 (0.86 g, 86%, white solid, mp: 95° C.), Elementary analysis: C=68.12%, H=11.18%

Workup

  1. extractionThe mixture was extracted with EtOAc (3×30 mL)
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography (SiO2, 3×10 cm, 25% Et2O-hexanes)
  6. customto give 8 (0.86 g, 86%, white solid, mp: 95° C.), Elementary analysis

Sources & evidence

ORD record
ord-466d564b0b3c41e9bf060764f7d0831e
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

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