Imidazole → tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silane

HRID 1583635Notes

Reaction equation

HRID 1583635 reaction equation
[OH:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:3]#[CH:4].N1C=CN=C1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].O>CN(C)C=O.CCCCCC>[Si:19]([O:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:3]#[CH:4])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 131661-Octyn-3-olHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11791325tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3-hydroxyoct-1-yne (see Preparation 3.A.) (2.89 g, 0.02 mol), in N,N-dimethylformamide (DMF), cooled to 0° C., was added imidazole (2.1 g), followed by tert-butyldimethylchlorosilane (3.1 g, 0.02 mol), and the mixture was stirred for 3 h. Water (80 ml) and hexane (80 ml) were added; the organic layer was separated and combined with 2×80 ml of hexane extractions of the aqueous layer. The solvent was removed (in vacuo), after drying over sodium sulfate, to give a crude residue (4.3 g) which was chromatographed on silica gel (80 g), eluting with ethyl acetate-hexane (2:1, v/v) to afford 3-tert-butyldimethylsilyloxyoct-1-yne. JACS, 94, 6190, (1972).

Workup

  1. customthe organic layer was separated
  2. extractioncombined with 2×80 ml of hexane extractions of the aqueous layer
  3. customThe solvent was removed (in vacuo)
  4. dry with materialafter drying over sodium sulfate
  5. customto give a crude residue (4.3 g) which
  6. customwas chromatographed on silica gel (80 g)
  7. washeluting with ethyl acetate-hexane (2:1, v/v)

Sources & evidence

ORD record
ord-dac94fc394be4872b790b8ab13dfdea7
Source dataset
uspto-grants-1985_11
Patent number
US04552898

Reaction notes

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