Trimethylsilylacetylene → 2H-Pyran-3-ol, tetrahydro-3-[2-(trimethylsilyl)ethynyl]-

HRID 1398533Notes

Reaction equation

HRID 1398533 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[Li]CCCC.[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14]>C1COCC1>[CH3:16][Si:15]([C:13]#[C:14][C:3]1([OH:7])[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 178418339Butyllithium

Product 1

HCID 681819602H-Pyran-3-ol, tetrahydro-3-[2-(trimethylsilyl)ethynyl]-Yield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of dihydro-2H-pyran-3(4H)-one (200 mg, 2 mmol) in THF was treated with n-BuLi (2 mL) at −78° C. for about 30 min. Ethynyltrimethylsilane (300 mg, 3 mmol) was then added and the reaction mixture was stirred for 3 hr. Purification by gel chromatography afforded the title compound (200 mg, 50%); 1H NMR (400 MHz, DMSO) delta 0.15 (s, 9H), 1.52-1.55 (m, 1H), 1.62-1.67 (m, 1H), 1.80-1.88 (m, 1H), 3.23-3.26 (m, 1H), 3.37-3.44 (m, 1H), 3.49-3.56 (m, 2H), 5.52 (s, 1H).

Workup

  1. customPurification by gel chromatography

Sources & evidence

ORD record
ord-63f99aa4c91742b6b17f37829f54d667
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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