Sodium Bicarbonate → HCID 10782713, compound

HRID 431291Notes

Reaction equation

HRID 431291 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[CH2:6][O:7][C:8]([O:10][C:11]1[C:18]([CH3:19])=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[CH3:20])=[O:9])([O-:3])=[O:2].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CCO>[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[CH2:6][O:7][C:8]([O:10][C:11]1[C:12]([CH3:20])=[CH:13][C:14]([CH2:15][OH:16])=[CH:17][C:18]=1[CH3:19])=[O:9])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10711411HCID 10711411, compound

Product 1

HCID 10782713HCID 10782713, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added EtOH (0.5 mL) at r.t. to a mixture of 7h (100 mg, 0.3 mmol) and sodium borohydride (12 mg, 0.3 mmol) and then refluxed for 5 minutes. Quenched reaction with 1 m HCl (0.5 mL) and poured into 5% NaHCO3 (15 mL). Aqueous workup (Et2O, MgSO4) followed by concentration in vacuo afforded a yellow oil which was purified by flash chromatography (20 g. 1:1 hexanes/ethyl acetate) to yield 8h (56 mg, 56%) as a crystalline solid: 1H NMR (270 MHz, (CDCl3) d 2.19 (s, 6H), 4.56 (s, 2H), 5.69 (s, 2H), 7.04 (s, 2H), 7.49-7.55 (m, 1H), 7.69-7.72 (m, 2H), 8.15 (d, J=7.9 Hz, 1H); 13C NMR (68 MHz, CDCl3) d 16.1, 64.7, 66.9, 125.4, 127.5, 128.8, 129.3, 130.3, 131.6, 134.1, 138.9, 147.3, 147.69, 152.7.

Workup

  1. temperaturerefluxed for 5 minutes
  2. customQuenched
  3. customreaction with 1 m HCl (0.5 mL)
  4. concentrationAqueous workup (Et2O, MgSO4) followed by concentration in vacuo
  5. customafforded a yellow oil which
  6. customwas purified by flash chromatography (20 g. 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f3775147094f450496c8e0da9658f258
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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