Acetone → HCID 18449571, compound

HRID 1270444Notes

Reaction equation

HRID 1270444 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH:13]1([C:19]#[N:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:21][C:22]([CH3:24])=[O:23]>C1COCC1.CCOCC>[OH:23][C:22]([C:13]1([C:19]#[N:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:24])[CH3:21]

Participants

7

Reactant 4

HCID 180AcetoneHCID 7912DiisopropylamineHCID 69834CyanocyclohexaneHCID 178418339Butyllithium

Product 1

HCID 18449571HCID 18449571, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (4.2 mL) in THF (30 mL) at 0° C. was added n-BuLi in hexanes (1.6 M, 19 mL). After stirring for 30 min., the reaction mixture was cooled to −78° C. and cyclohexanecarbonitrile (1.09 g, 10 mmol) in THF (10 mL) was added drop wise. After 2 h, acetone (1.16 g, 20 mmol) was added. The reaction mixture was stirred from −78° C. to rt overnight, diluted with Et2O (100 mL), washed with 1N HCl, H2O, brine and dried over anhydrous sodium sulfate. Purification by flash chromatography (1:1, hexanes-Et2O) gave 1-(1-hydroxy-1-methyl-ethyl)-cyclohexanecarbonitrile (1.27 g, 76%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ (ppm) 0.86–1.91 (8H, m), 1.35 (6H, s), 2.01 (2H, d, J=12.8 Hz), 3.65 (1H, t, J=6.4 Hz). Mass Spec [M+H]+=168.1.

Workup

  1. waitAfter 2 h
  2. stirringThe reaction mixture was stirred from −78° C. to rt overnight
  3. washwashed with 1N HCl, H2O, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customPurification by flash chromatography (1:1, hexanes-Et2O)

Sources & evidence

ORD record
ord-3cc750028d724b4d8629b80f75e6a8d2
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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