Allyltrimethylsilane → HCID 68855046, compound

HRID 2101649Notes

Reaction equation

HRID 2101649 reaction equation
[CH2:1]([C@H:8]([CH:12]=[CH2:13])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([Si:17]([CH3:20])([CH3:19])[CH3:18])C=C>C(Cl)Cl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH2:1]([C@H:8]([CH:12]=[CH:13][CH2:14][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 69808AllyltrimethylsilaneHCID 10899197HCID 10899197, compound

Product 1

HCID 68855046HCID 68855046, compound

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-benzylbut-3-enoic acid (1.4 mmol, 250 mg) and allyltrimethylsilane (4.2 mmol, 0.67 mL) in DCM (3 mL) at reflux was added Hoveyda-Grubbs second generation catalyst (5 mol %, 44 mg). The reaction was allowed to stir at reflux for 50 hrs. The solvent was removed in vacuo. The crude product was purified by column chromatography (184 mg, 50%). 1H NMR (400 MHz, CDCl3): δ=7.15-7.30 (m, 5H), 5.48-5.56 (m, 1H), 5.26 (dd, J=8.8, 15.2, 1H), 3.30 (m, 1H), 3.10 (dd, J=7.1, 13.9, 1H), 2.80 (dd, J=7.8, 13.6, 1H), 1.43 (d, J=8.3, 2H), −0.08 (s, 9H); 13C NMR (125 MHz, CDCl3): δ=179.5, 138.7, 131.4, 130.1, 129.1, 129.0, 128.3, 126.4, 126.3, 124.3, 123.7, 50.8, 38.5, 22.9, 18.9, −2.08; IR (CHCl3): v 2955, 1797; HMRS required for C15H21O2Si ([M−H]−) 261.1311 found 261.1318; [α]D21=−39.4 (c, 0.5, CHCl3).

Workup

  1. temperatureat reflux for 50 hrs
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by column chromatography (184 mg, 50%)

Sources & evidence

ORD record
ord-3fe4bdfc732144b399593e2b6c15615d
Source dataset
uspto-grants-2009_08
Patent number
US07572928B2

Reaction notes

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