Triphenylphosphine → HCID 53637259, compound

HRID 2228344Notes

Reaction equation

HRID 2228344 reaction equation
[CH:1]#[C:2][CH:3]([OH:5])C.C1(P([C:19]2[CH:24]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([SiH:27]([CH2:30]C)[CH2:28][CH3:29])[CH3:26]>C(OC(=O)C)C>[CH2:25]([Si:27]([CH2:24][CH3:19])([CH2:28][CH3:29])[CH:30]=[CH:1][CH2:2][CH2:3][OH:5])[CH3:26]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 12052TriethylsilaneHCID 162393-Butyn-2-ol

Product 1

HCID 53637259HCID 53637259, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 50 ml reaction flask was charged with 1-butyne-3-ol and a catalytic amount of bis(1,5-cyclooctadiene)-di-Rh(I)-dichloride and triphenylphosphine under an inert atmosphere. Triethylsilane was slowly added to the reaction flask through a dropping funnel. The reaction mixture was stirred at room temperature for 72 hours and then concentrated at the rotary evaporator. The product was chromatographed through SiO2 in a hexane:ethylacetate solution (95:5 to 70:30) to yield 86% of a yellow liquid. Purity according to gas chromatography was 96% trans and 3.4% cis product.

Workup

  1. customA 50 ml reaction flask
  2. concentrationconcentrated at the rotary evaporator
  3. customThe product was chromatographed through SiO2 in a hexane

Sources & evidence

ORD record
ord-b9c3acee4116401aaa5e2fd680932f92
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

Loading…