HCID 586422, compound → HCID 18345115, compound

HRID 2301808Notes

Reaction equation

HRID 2301808 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:2]1.C(O[CH2:16][C:17]([CH2:19][Si](C)(C)C)=[CH2:18])(=O)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:16]=[C:17]1[CH2:19][C@@H:7]([C:8]([O:10][CH3:11])=[O:9])[C@H:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH2:18]1

Participants

6

Reactant 2

HCID 586422HCID 586422, compoundHCID 44283472-(Trimethylsilylmethyl)allyl acetate

Product 1

HCID 18345115HCID 18345115, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 742671,2-Bis(diphenylphosphino)ethaneCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-(3-thienyl)acrylate (10.0 g, 59.5 mmol), tetrakis(triphenylphosphine)palladium(0) (5.15 g, 5.6 mmol), 1,2-bis(diphenylphosphino)ethane (1.35 g, 3.4 mmol) and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (20 g, 107 mmol) in THF (125 mL) under argon was heated to reflux for 24 h. The volatiles were then removed in vacuo and the residue was purified by FC (5% ethyl acetate in hexanes) to afford the title compound (11.4 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. customThe volatiles were then removed in vacuo
  4. customthe residue was purified by FC (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1d6328c4150647ce88b53e43f8d74cd4
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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