Water → HCID 66760949, compound

HRID 1850416Notes

Reaction equation

HRID 1850416 reaction equation
[CH3:1][S-:2].[Na+].CC(N(C)C)=O.[Br:10][C:11]1[C:12]([CH3:25])=[C:13]([CH3:24])[C:14]2[O:18][C:17]([CH2:20]I)([CH3:19])[CH2:16][C:15]=2[C:22]=1[CH3:23].O>C(OCC)(=O)C>[Br:10][C:11]1[C:12]([CH3:25])=[C:13]([CH3:24])[C:14]2[O:18][C:17]([CH3:19])([CH2:20][S:2][CH3:1])[CH2:16][C:15]=2[C:22]=1[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 4378561Sodium methanethiolateHCID 66760191HCID 66760191, compound

Product 1

HCID 66760949HCID 66760949, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

Sodium thiomethoxide (213 mg, 3.03 mmol) was added to a solution of DMA (3 mL) containing 5-bromo-2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (270 mg, 0.683 mmol) synthesized in Reference Example 133, and the mixture was stirred at 140° C. for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate an organic layer. The organic layer was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0-90:10) to give 130 mg of the title compound (yield: 68%).

Workup

  1. customsynthesized in Reference Example 133
  2. temperatureThe reaction solution was cooled to room temperature
  3. customto separate an organic layer
  4. washThe organic layer was washed with saturated saline
  5. customdried
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0-90:10)

Sources & evidence

ORD record
ord-4e9989d86d8b4e9f9fc81bb1abe83e31
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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