Potassium Carbonate → HCID 54230199, compound

HRID 1395080Notes

Reaction equation

HRID 1395080 reaction equation
[CH:1]([C@@:3]1([CH3:10])[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1)=O.[Cl-].[CH3:12][O:13][C:14]1[C:39]([CH3:40])=[C:38]([CH3:41])[C:37]([O:42][CH3:43])=[C:36]([CH3:44])[C:15]=1[CH2:16][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[CH3:43][O:42][C:37]1[C:38]([CH3:41])=[C:39]([CH3:40])[C:14]([O:13][CH3:12])=[C:15]([CH3:16])[C:36]=1[CH:44]=[CH:1][C@@:3]1([CH3:10])[CH2:7][O:6][C:5]([CH3:8])([CH3:9])[O:4]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11423659HCID 11423659, compoundHCID 86736520HCID 86736520, compound

Product 1

HCID 54230199HCID 54230199, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

1.84 g of (R)-4-formyl-2,2,4-trimethyl-1,3-dioxolan, 11.0 g of 2,5-dimethoxy-3,4,6-trimethylbenzyl-triphenylphosphonium chloride and 3.3 g of finely ground anhydrous potassium carbonate were heated at reflux for 30 hours in 25 ml of dry acetonitrile (dried over phosphorus pentoxide and distilled over potassium carbonate) in the presence of 55 mg of 18-crown-6 (1,4,7,10,13,16-Hexa-oxo-cyclooctadecane) the suspension being vigorously stirred. Thereupon, the brown suspension was chromatographed on 400 g of silica gel with toluene-methyl acetate-pentane (20:3:3 parts by volume) as the elution agent. After bulb-tube distillation at 170° (bath temperature)/0.2 mmHg, there were obtained 2.57 g of (S)-4-(2,5-dimethoxy-3,4,6-trimethyl-styryl)-2,2,4-trimethyl-1,3-dioxolan as a colorless viscous oil; [α]D20 =+17.9° (c=2.1 in chloroform).

Workup

  1. customThereupon, the brown suspension was chromatographed on 400 g of silica gel with toluene-methyl acetate-pentane (20:3:3 parts by volume) as the elution agent
  2. distillationAfter bulb-tube distillation at 170° (bath temperature)/0.2 mmHg

Sources & evidence

ORD record
ord-c2538f2939914a2cbe75dbf106836710
Source dataset
uspto-grants-1980_05
Patent number
US04201879

Reaction notes

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