HCID 9909120, compound → HCID 15542188, compound

HRID 1421077Notes

Reaction equation

HRID 1421077 reaction equation
Br[CH2:2][CH:3]([CH3:23])[O:4][C:5]1[C:6](=[O:22])[O:7][C:8]([CH3:21])([CH3:20])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CC(C)([O-])C.[K+]>C1COCC1>[C:3]([O:4][C:5]1[C:6](=[O:22])[O:7][C:8]([CH3:21])([CH3:20])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1)([CH3:23])=[CH2:2]

Participants

4

Reactant 2

HCID 9909120HCID 9909120, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15542188HCID 15542188, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the bromide of Example 6 (300 mg, 0.746 mmol) in THF (10 mL) was added 1.5 mL of a 1M THF solution of potassium tert-butoxide. The resulting mixture was stirred at room temperature for 1 h. The reaction mixture was then partitioned between 25% NH4OAc and EtOAc. The organic phase was dried over Na2SO4, filtered and evaporated. After flash chromatography, 100 mg of the title compound was obtained.

Workup

  1. customThe reaction mixture was then partitioned between 25% NH4OAc and EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3526d8be2649495291b5019fb2a27c60
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

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