Bicyclo(2.2.1)heptan-2-one → 2-((Trimethylsilyl)ethynyl)bicyclo[2.2.1]heptan-2-ol

HRID 1398531Notes

Reaction equation

HRID 1398531 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=[O:8].[Li]CCCC.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>C1COCC1>[CH3:17][Si:16]([C:14]#[C:15][C:2]1([OH:8])[CH2:3][CH:4]2[CH2:7][CH:1]1[CH2:6][CH2:5]2)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 66111TrimethylsilylacetyleneHCID 178418339Butyllithium

Product 1

HCID 700746122-((Trimethylsilyl)ethynyl)bicyclo[2.2.1]heptan-2-olYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bicyclo[2.2.1]heptan-2-one (1.1 g, 10 mmol) in THF was treated with n-BuLi (6 mL, 2.5 M in n-hexane) at −78° C. for about 30 min. Ethynyltrimethylsilane (1.1 g, 11 mmol) was then added and the reaction mixture was stirred for 3 hr. Purification by gel chromatography afforded the title compound (1.6 g); 1H NMR (400 MHz, DMSO) delta 0.16 (s, 9H), 1.15-1.44 (m, 4H), 1.64-1.67 (m, 1H), 1.88-1.93 (m, 2H), 2.07-2.22 (m, 3H), 3.94 (s, 1H).

Workup

  1. customPurification by gel chromatography

Sources & evidence

ORD record
ord-0f63b099f42e4faf9336a7b57d709f3f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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