Potassium Carbonate → Tert-butyl-(2,2-dimethyl-but-3-ynyloxy)-dimethyl-silane

HRID 1398536Notes

Reaction equation

HRID 1398536 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:15]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([Si:5]([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[C:9]#[CH:15])([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106563753-((Tert-butyldimethylsilyl)oxy)-2,2-dimethylpropanalHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86669580Tert-butyl-(2,2-dimethyl-but-3-ynyloxy)-dimethyl-silaneYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propionaldehyde (0.84 g, 3.9 mmol) in methanol (20 mL) was added (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (0.9 g, 4.7 mmol) and K2CO3 (1.1 g, 7.8 mmol). The solution was stirred overnight at room temperature and then the reaction mixture was washed with water. The crude residue was purified by flash chromatography (eluted with: petroleum ether:EtOAc=100:2) to afford the title compound (0.17 g, 21%): 1H NMR (CDCl3, 400 MHz) delta 0.05 (s, 6H), 0.90 (s, 9H), 1.19 (s, 6H), 2.06 (s, 1H), 3.45 (s, 2H).

Workup

  1. washthe reaction mixture was washed with water
  2. customThe crude residue was purified by flash chromatography (eluted with: petroleum ether:EtOAc=100:2)

Sources & evidence

ORD record
ord-bc668b3eba9142aea16c32be42f45ac8
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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