Methyl iodide → HCID 69115252, compound

HRID 916541Notes

Reaction equation

HRID 916541 reaction equation
[CH3:1][C:2]([N:8]1[Si:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][Si:9]1([CH3:16])[CH3:15])([CH3:7])[C:3]#[C:4][CH2:5][OH:6].[K].[CH3:18][Si]([NH-])(C)C.CI>O1CCCC1.O>[CH3:18][O:6][CH2:5][C:4]#[C:3][C:2]([N:8]1[Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][Si:12]1([CH3:13])[CH3:14])([CH3:1])[CH3:7]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 5462222PotassiumHCID 21078360HCID 21078360, compoundHCID 53627528(Trimethylsilyl)amide

Product 1

HCID 69115252HCID 69115252, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-Methyl-4-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)pent-2-yn-1-ol (2.55 g) in dry tetrahydrofuran (30 ml) was cooled to −10° C. under an atmosphere of nitrogen with stirring and potassium bis(trimethylsilylamide (2.09 g) in dry tetrahydrofaran (25 ml) was added over 5 minutes then the mixture was stirred at −(10 to 5)° C. for 0.75 hours. Methyl iodide (1.49 g) in tetrahydrofuran (10 ml) was added over 5 minutes and the mixture was allowed to warm to ambient temperature over 2 hour then stored for 18 hours. The mixture was diluted with water and extracted with ethyl acetate (three times). The extracts were combined, washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give 1-(1-methoxy-4-methylpent-2-yn-4-yl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane as a yellow liquid. This liquid was stirred with dilute aqueous hydrochloric acid (30 ml) for 0.25 hours, washed with diethyl ether (twice) and the aqueous acidic phase separated then evaporated under reduced pressure. The residue was evaporated under reduced pressure with toluene (twice) to remove any water, dissolved in dichloromethane and dried over magnesium sulphate then evaporated under reduced pressure to give 4-amino-1-methoxy-4-methylpent-2-yne hydrochloride, 0.66 g, as a pale yellow solid.

Workup

  1. stirringthe mixture was stirred at −(10 to 5)° C
  2. waitthen stored for 18 hours
  3. extractionextracted with ethyl acetate (three times)
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-605b1196905a49c6adb52095c5e245c4
Source dataset
uspto-grants-2007_09
Patent number
US07271130B2

Reaction notes

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