Sodium Sulfate → HCID 58380984, compound

HRID 45199Notes

Reaction equation

HRID 45199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:18]=[N:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:26]([Mg]Br)=[CH2:27].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:18]([NH:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH:26]=[CH2:27])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 67075469HCID 67075469, compoundHCID 178418507HCID 178418507, compound2×

Product 1

HCID 58380984HCID 58380984, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 2.00 g (5.44 mmol) of 2-methyl-propane-2-sulfinic acid 8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-ylmethyleneamide (105) were dissolved in 27 mL of absolute tetrahydrofuran. Then, 5.99 mL (5.99 mmol) of vinylmagnesium bromide (1M in tetrahydrofuran) were added dropwise at 0° C. and the reaction mixture was stirred for 17 h at room temperature. Another 3 mL (3.00 mmol) of vinylmagnesium bromide (1M in tetrahydrofuran) were added and the mixture stirred for 20 h at room temperature. The reaction mixture was cooled to 0° C. and 15 mL of saturated aqueous sodium sulphate solution were added. The suspension was filtered over celite, the organic layer was dried over magnesium sulphate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane) to yield 1.09 g of (106). Rt=0.96 min (Method 18). Detected mass: 396.4 (M+H+).

Workup

  1. stirringthe mixture stirred for 20 h at room temperature
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationThe suspension was filtered over celite
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-d066351279954d9ab020c79276c53f0b
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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