Trimethylsilylacetylene → 2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-trimethylsilanylethynyltetrahydro-pyran-4-ol
Reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[Li]CCCC.[C:12]([SiH2:16][O:17][C:18]([CH3:27])([CH3:26])[CH:19]1[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][O:20]1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([SiH2:16][O:17][C:18]([CH3:27])([CH3:26])[CH:19]1[CH2:24][C:23]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])([OH:25])[CH2:22][CH2:21][O:20]1)([CH3:15])([CH3:13])[CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A cold (−78 ° C.), stirred solution of (trimethylsilyl)acetylene (1.01 g, 10.3 mmol) in anhydrous THF (25 mL) was treated with nBuLi (4.12 mL in hexane, 10.3 mmol) under nitrogen. The colorless solution was stirred for 30 minutes and followed by the addition of 2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-one (1.48 g, 6.06 mmol) in anhydrous THF (25 mL). The reaction was warmed up to room temperature, stirred for 2 hours, and quenched with water (30 mL). After removal of THF, the product was extracted with EtOAc (2×50 mL). The combined organic layer was washed with brine, dried over sodium sulfate, and concentrated to give 1.75 g (84%) of yellow oil: 1H NMR (CDCl3) δ 0.05 (s, 6H), 0.16 (s, 9H), 0.89 (s, 9H), 1.43 (m, 1H), 1.78 (td, 1H), 1.83 (d, 1H), 1.94 (d, 1H), 3.52-3.70 (m, 4H), 4.00 (m 1H).
Workup
- stirringstirred for 2 hours
- customquenched with water (30 mL)
- customAfter removal of THF
- extractionthe product was extracted with EtOAc (2×50 mL)
- washThe combined organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cd644ff6780d4642a52e1a3d0e498cd2
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06284764B1
Reaction notes
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