Water → HCID 20086763, compound

HRID 1608557Notes

Reaction equation

HRID 1608557 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[C:3]=1[N+:23]([O-:25])=[O:24].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[CH:13][CH:12]=2)[C:3]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 12052Triethylsilane2×HCID 20086785HCID 20086785, compound

Product 1

HCID 20086763HCID 20086763, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from step (b) (11.1 g) in trifluoroacetic acid (16 ml) was stirred at room temperature and triethylsilane (12.5 ml) added. The mixture was stirred overnight at room temperature, followed by 3 hours at 50° C. during which further portions of triethylsilane (3 ml each) were added after 1.5 hours and 2.5 hours, then poured into water (250 ml). The latter was extracted with ether (×2) and the combined extracts washed with water (×2), dried over MgSO4, and evaporated under reduced pressure to give an oil which was flash chromatographed through a silica column using ether/hexane (1:4v/v). The eluate was evaporated under reduced pressure to give 11.0 g of the desired product.

Workup

  1. additionwere added after 1.5 hours and 2.5 hours
  2. extractionThe latter was extracted with ether (×2)
  3. washthe combined extracts washed with water (×2)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give an oil which
  7. customchromatographed through a silica column
  8. customThe eluate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-44a64cdb588344849972137732f71330
Source dataset
uspto-grants-1995_03
Patent number
US05395853

Reaction notes

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