Diethyl Ether → 4-Dimethylamino-4-(thiophen-2-yl)-1-(5-(triethylsilyl)pent-4-inyl)cyclohexanol

HRID 2064529Notes

Reaction equation

HRID 2064529 reaction equation
C([Li])(C)(C)C.CCCCC.[CH2:11]([Si:13]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:14]#[C:15][CH2:16][CH2:17][CH2:18]I)[CH3:12].[CH3:24][N:25]([CH3:37])[C:26]1([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[Cl-].[NH4+].C([O:42]CC)C>>[CH3:24][N:25]([CH3:37])[C:26]1([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[CH2:27][CH2:28][C:29]([CH2:18][CH2:17][CH2:16][C:15]#[C:14][Si:13]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:11][CH3:12])([OH:42])[CH2:30][CH2:31]1

Participants

7

Reactant 6

HCID 3283Diethyl Ether2×HCID 8003PentaneHCID 25517Ammonium ChlorideHCID 686314624-Dimethylamino-4-(thiophen-2-yl)cyclohexaneHCID 131729988HCID 131729988, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 1317299914-Dimethylamino-4-(thiophen-2-yl)-1-(5-(triethylsilyl)pent-4-inyl)cyclohexanol

Procedure

In a heated apparatus a 1.7 M solution of tert-butyl lithium in pentane (22.3 mL, 37.9 mmol) was slowly added in drops to a solution of triethyl-(5-iodopent-1-inyl)silane (5.64 g, 18.9 mmol) in absolute diethyl ether (50 mL) at an inside temperature of −70° C. to −75° C. with argon. After 120 min at this temperature a solution of 4-dimethylamino-4-(thiophen-2-yl)cyclohexane (4.22 g, 18.9 mmol) in absolute diethyl ether (100 mL) was slowly added in drops and subsequently stirred for 30 min. The reaction solution was then heated to room temperature and mixed with saturated ammonium chloride solution (100 mL). The phases were separated and the aqueous phase extracted with diethyl ether (3×50 mL). The combined organic phases were washed with saturated sodium chloride solution (50 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (7.02 g) was purified by means of flash chromatography (100 g, 20×4.0 cm) with cyclohexane /ethyl acetate (2:1).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with diethyl ether (3×50 mL)
  3. washThe combined organic phases were washed with saturated sodium chloride solution (50 mL)
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated to low volume in a vacuum
  6. customThe residue (7.02 g) was purified by means of flash chromatography (100 g, 20×4.0 cm) with cyclohexane /ethyl acetate (2:1)

Sources & evidence

ORD record
ord-d461789a9d1d41458720c7bd5e41c815
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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