Water → Isohexane ethyl acetate

HRID 496657Notes

Reaction equation

HRID 496657 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9]C2C=CN=C(SC)N=2)[CH:5]=C[CH:7]=1.C[Si]([C:23]#[CH:24])(C)C.C(NC(C)C)(C)C.[OH2:32]>C1COCC1>[CH3:7][CH2:2][CH2:3][CH:4]([CH3:8])[CH3:5].[C:23]([O:18][CH2:8][CH3:9])(=[O:32])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 22322021HCID 22322021, compound

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16.3 g (44.0 mmol) C2 in 260 ml dry THF at 10° C. under nitrogen 1.5 g (2.2 mmol) bis-(triphenylphosphine)palladium-II-chloride, 900 mg (4.7 mmol) copper-I-iodide, 12 ml (85 mmol) trimethylsilylacetylene and 30 ml diisopropylamine were added and the mixture was stirred and successively allowed to warm up to room temperature. After stirring at room temperature overnight, 260 ml water were added and the mixture was extracted twice with ether. The organic layer was separated, dried and evaporated to dryness. Column chromatography of the residue on SiGel (iso-hexane/ethyl acetate 3:1) yielded 12.5 g (83%) C17.

Workup

  1. stirringAfter stirring at room temperature overnight
  2. extractionthe mixture was extracted twice with ether
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7787a09974d74b7a966870378f4d279e
Source dataset
uspto-grants-2005_09
Patent number
US06946471B2

Reaction notes

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