Ammonium Chloride → [6-(4-Methoxy-phenyl)-hex-1-ynyl]-trimethyl-silane

HRID 1768049Notes

Reaction equation

HRID 1768049 reaction equation
C([Li])CCC.[CH3:6][Si:7]([C:10]#[CH:11])([CH3:9])[CH3:8].CN1C(=O)N(C)CCC1.I[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][CH2:23][CH2:22][C:11]#[C:10][Si:7]([CH3:9])([CH3:8])[CH3:6])=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 2848841-(4-Iodobutyl)-4-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 23614554[6-(4-Methoxy-phenyl)-hex-1-ynyl]-trimethyl-silaneYield 124.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

12.4 ml (19.8 mmol) of 1.6 M butyllithium in n-hexane was added dropwise at −78° C. to a solution of 1.94 g (2.80 ml, 19.8 mmol) trimethylsilylacetylene and 2.39 ml(19.8 mmol) DMPU in 30 ml THF. After stirring for 1 h at −78° C. a solution of 28.7 g (9.89 mmol) 1-(4-Iodo-butyl)-4-methoxy-benzene in ml THF was added at −78° C. and stirring continued for 30 min. The reaction mixture was allowed to warm to r.t. overnight and then hydrolyzed by a saturated ammonium chloride solution. The water phase was extracted with ether and the combined organic phases were dried over sodium sulphate. Removal of solvents in vacuo gave 3.20 g yellow liquid, which still contained solvent and was used without further purification.

Workup

  1. additionwas added at −78° C.
  2. extractionThe water phase was extracted with ether
  3. dry with materialthe combined organic phases were dried over sodium sulphate
  4. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-7b511033b4a640fa9e941f698a23ef79
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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