Water → HCID 59637737, compound

HRID 1892019Notes

Reaction equation

HRID 1892019 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:8].[K].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.C(Cl)(Cl)Cl.O>CN(C=O)C>[C:18]1(=[O:28])[N:22]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])[C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 24194345Phthalimide potassium saltHCID 59637735HCID 59637735, compound

Product 1

HCID 59637737HCID 59637737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(trimethylsilyl)prop-2-ynyl 6-bromohexanoate (0.606 g, 2 mmol, 1 eq.) was added to a solution of phthalimide potassium salt (0.4412 g, 2.4 mmol, 1.2 eq.) in 50 mL of DMF and stirred overnight under argon. CHCl3 was added to the solution flask and was transferred to a separatory funnel containing water. The aqueous layer was separated and twice extracted with CHCl3. The combined organic layers were twice extracted with water then the solvent was removed on a rotary evaporator. Remaining solvent was removed under high vacuum overnight to yield a brown oil.

Workup

  1. customwas transferred to a separatory funnel
  2. customThe aqueous layer was separated
  3. extractiontwice extracted with CHCl3
  4. extractionThe combined organic layers were twice extracted with water
  5. customthe solvent was removed on a rotary evaporator
  6. customRemaining solvent was removed under high vacuum overnight
  7. customto yield a brown oil

Sources & evidence

ORD record
ord-1ca5145ce0074dfaa3e8a06dbd24ecd4
Source dataset
uspto-grants-2013_08
Patent number
US08507572B2

Reaction notes

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