Tetrahydrofuran → HCID 86071681, compound

HRID 1466034Notes

Reaction equation

HRID 1466034 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O=[C:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]#[N:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.C1[CH2:27][O:26][CH2:25]C1>>[CH3:25][O:26][CH:27]=[C:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]#[N:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 3128961-oxo-2,3-dihydro-1H-indene-5-carbonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 86071681HCID 86071681, compound

Conditions

Temperature
0 °C

Procedure

To a mixture of CH3OCH2PPh3I (8.9 g, 26 mmol) in THF (80 mL) was added a solution of NaHMDS in THF (2.0M, 13 mL, 26 mmol)) at 0° C. The mixture was stirred 1 hour at 0° C. Then a solution of 1-Oxoindane-5-carbonitrile (2.0 g, 13 mmol) in THF (10 mL) was added. The mixture was stirred for 2 hours at 0° C. The reaction was quenched with water and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatograph to give the title compound. MS m/z: 186 [M+1]+.

Workup

  1. stirringThe mixture was stirred for 2 hours at 0° C
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatograph

Sources & evidence

ORD record
ord-58342708b902474b9faef8ce39a3b550
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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