Imidazole → HCID 12164634, compound

HRID 250532Notes

Reaction equation

HRID 250532 reaction equation
[CH:1]#[C:2][CH:3]([OH:8])[CH2:4][CH2:5][CH2:6][CH3:7].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[NH4+].[Cl-]>CN(C=O)C.C(OCC)(=O)C>[C:17]([Si:14]([O:8][CH:3]([CH2:4][CH2:5][CH2:6][CH3:7])[C:2]#[CH:1])([CH3:16])[CH3:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 930501-Heptyn-3-ol

Product 1

HCID 12164634HCID 12164634, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of hept-1-yn-3-ol (5.0 g, 0.0446 mol) in dry DMF (50 mL) were added imidazole (3.64 g, 0.054 mol) and tert-butyldimethylsilyl chloride (6.06 g, 0.054 mol). The resulting mixture was stirred at RT for 18 h and then treated with saturated NH4Cl (25 mL) and ethyl acetate (250 mL). The organic layer was washed with saturated NH4Cl (50 mL), water (4×100 mL), brine (2×100 mL), dried over sodium sulfate, and concentrated in vacuo to afford the crude product (9.57 g, 95%), as a yellow oil, which was used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.09 (s, 3H), 0.12 (s, 3H), 0.89 (s, 9H), 1.31-1.38 (m, 4H), 1.65-1.67 (m, 2H), 3.35 (s, 1H), 4.32-4.33 (m, 1H).

Workup

  1. washThe organic layer was washed with saturated NH4Cl (50 mL), water (4×100 mL), brine (2×100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e08f7019605494caa6f9b58dbfcceb0
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

Loading…