2,2-Dimethoxypropane → HCID 20077579, compound

HRID 1655075Notes

Reaction equation

HRID 1655075 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8](O)(=O)=O)=[CH:4]C=1.[F-].[CH2:14]([N+:18](CCCC)(CCCC)CCCC)CCC.[C:31](=O)(O)[O-].[Na+].[CH3:36][O:37][C:38]([O:41]C)([CH3:40])[CH3:39]>C1COCC1>[CH2:2]([CH:7]1[CH2:36][O:37][C:38]([CH3:40])([CH3:39])[O:41][CH:6]1[C:5]1[S:8][CH:14]=[N:18][CH:4]=1)[CH:12]=[CH2:31]

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 20077579HCID 20077579, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Toluenesulphonic acid monohydrate (13.4 g) was added to a solution of compound B (20.0 g) in 2,2-dimethoxypropane (100 ml) and the mixture was stirred for 18 hours at ambient temperature. A 1M solution of tetrabutylammonium fluoride in THF (150 ml) was then added and the mixture stirred for a further 15 minutes. The reaction mixture was then neutralised with excess saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated and the residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), to give (4RS,5RS)-5-allyl-2,2-dimethyl-4-(5-thiazolyl)-1,3-dioxane (C) (13.0 g; 85% yield) as an oil; NMR: 1.45-1.55(6H,m), 1.6-2.05 and 2.4-2.5(3H,m), 3.68-4.16(2H,m), 4.9-5.1 and 5.5-5.72(4H,m), 7.72 and 7.81(isomers, 1H,2s), 8.72 and 8.79(isomers, 1H,2s).

Workup

  1. stirringthe mixture stirred for a further 15 minutes
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography
  6. washeluting with 25% ethyl acetate/hexane (v/v)

Sources & evidence

ORD record
ord-b75ffab7e49046cea25717d07b469250
Source dataset
uspto-grants-1995_04
Patent number
US05410064

Reaction notes

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