Sodium Bicarbonate → HCID 86758797, compound

HRID 1634626Notes

Reaction equation

HRID 1634626 reaction equation
[CH3:1][CH:2]([CH2:28][CH3:29])[C:3]([O:5][CH:6]1[CH:15]2[C:10]([CH:11]=[CH:12][CH:13]([CH3:26])[CH:14]2[CH2:16][CH2:17][CH:18]2[CH2:23][CH:22]([OH:24])[CH2:21][CH:20]([OH:25])[O:19]2)=[CH:9][CH:8]([CH3:27])[CH2:7]1)=[O:4].[C:30](=O)(O)[O-].[Na+]>CO.C(Cl)(=O)C>[CH3:1][CH:2]([CH2:28][CH3:29])[C:3]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:26])[C:14]=2[CH2:16][CH2:17][CH:18]2[CH2:23][CH:22]([OH:24])[CH2:21][CH:20]([O:25][CH3:30])[O:19]2)[CH:9]=[C:8]([CH3:27])[CH:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 14164059HCID 14164059, compound

Product 1

HCID 86758797HCID 86758797, compoundYield 393.1%

Reagents, catalysts & solvents 2

HCID 6367Acetyl chlorideCatalystHCID 887MethanolSolvent

Procedure

Acetyl chloride (200 μL, 2.8 mmol) was added to a stirred solution of hemiacetals II (19.0 g, 46.7 mmol) in methanol (100 ml). The solution was stirred for 15 min at ambient temperature. Sodium bicarbonate (1.0 g) was added and the mixture was stirred for another 15 min. The mixture was filtered through a pad of Celite (5.5×1 cm) and washed with toluene. Evaporation of solvent of the filtrate gave crude acetals III (19.4 g, yield 98%) as a colorless syrup (HPLC purity >95%). This was used without further purification in the next step.

Workup

  1. stirringthe mixture was stirred for another 15 min
  2. filtrationThe mixture was filtered through a pad of Celite (5.5×1 cm)
  3. washwashed with toluene
  4. customEvaporation of solvent of the filtrate

Sources & evidence

ORD record
ord-7cb2888d57654438ae859c933b51cbc7
Source dataset
uspto-grants-2003_01
Patent number
US06506929B1

Reaction notes

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