Water → Isohexane ethyl acetate

HRID 1006479Notes

Reaction equation

HRID 1006479 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-9b158a8965cd4bed9af28f7ab3aed583
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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