Dimethyl Sulfoxide → HCID 67958670, compound

HRID 527601Notes

Reaction equation

HRID 527601 reaction equation
[H-].[Na+].[CH3:3][C:4]([Si:7]([CH3:28])([CH3:27])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][O:18][CH3:19])[C:11]=1[C:20](=[CH2:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:6])[CH3:5].[CH3:29]S(C)=O>>[CH3:3][C:4]([Si:7]([CH3:27])([CH3:28])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][O:18][CH3:19])[C:11]=1[C:20]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:29][CH2:26]1)([CH3:5])[CH3:6]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 67958380HCID 67958380, compound2×

Product 1

HCID 67958670HCID 67958670, compound

Procedure

NaH 60% disp in mineral oil (140 mg, 3.49 mmol) was added and the reaction mixture was stirred for 30 minutes at room temperature. A solution of ethyl 2-(2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-{[(methyloxy)methyl]oxy}phenyl)-2-propenoate (Intermediate 132, 830 mg) in dry dimethyl sulfoxide (5 mL) was added and the reaction mixture was stirred for 30 minutes at room temperature The reaction was quenched with ice, diluted with brine (10 ml) and water (10 ml) and extracted with ethyl acetate (2×30 ml). The organic layer was washed with water (3×15 ml) and brine (1×20 ml), dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 50 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 7:3 as eluent. This afforded the title compound as a colourless oil (780 mg).

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes at room temperature The reaction
  2. customwas quenched with ice
  3. additiondiluted with brine (10 ml) and water (10 ml)
  4. extractionextracted with ethyl acetate (2×30 ml)
  5. washThe organic layer was washed with water (3×15 ml) and brine (1×20 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 50 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 7:3 as eluent

Sources & evidence

ORD record
ord-05455163d6aa4b31a9128cda179fa9f3
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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