Hexane → HCID 58906751, compound

HRID 1432819Notes

Reaction equation

HRID 1432819 reaction equation
[CH2:1]([CH:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6]1)[CH2:2][C:3]#[CH:4].CN1C(=O)N(C)CCC1.[Li][CH2:22][CH2:23][CH2:24][CH3:25].CCCCCC>C1COCC1>[CH:24]1([CH2:25][C:4]#[C:3][CH2:2][CH2:1][CH:5]2[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6]2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 58906755HCID 58906755, compoundHCID 178418339Butyllithium

Product 1

HCID 58906751HCID 58906751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-But-3-ynyl-2,2-dimethyl-[1,3]dioxolane (6 mmol, 1.0 g) in 40 ml anhydrous THF and anhydrous DMPU (26 mmol, 3 g) was added a solution of 2.5M BuLi in hexane (9.01 mmol, 3.6 mL) at −78° C. It was stirred at −78° C. for 15 minutes and slowly warmed up to room temperature. The reaction mixture was quenched with sat. NH4Cl and extracted by EtOAc. The combined organic layer was washed with H2O and brine, dried by MgSO4 and concentrated. Silica gel chromatography (2˜10% EtOAc/Hexane) 4-(5-Cyclopropyl-pent-3-ynyl)-2,2-dimethyl-[1,3]dioxolane as a clear oil; 1H NMR (400 MHz, CDCl3): δ 4.22-5.15 (m, 1H), 4.07 (dd, 1H, J1=8.0 Hz, J2=6.0 Hz), 3.57 (dd, 1H, J1=7.9 Hz, J2=7.1 Hz), 2.29-2.23 (m, 2H), 2.20-2.16 (m, 2H), 1.83-1.77 (m, 1H), 1.72-1.65 (m, 1H), 1.40 (s, 3H), 1.35 (s, 3H), 0.91-0.86 (m, 1H), 0.46-0.41(m, 2H), 0.21-0.17 (m, 2H).

Workup

  1. temperatureslowly warmed up to room temperature
  2. customThe reaction mixture was quenched with sat. NH4Cl
  3. extractionextracted by EtOAc
  4. washThe combined organic layer was washed with H2O and brine
  5. dry with materialdried by MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dc176752ba22453b8342b680f816110c
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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