Sodium hydride → HCID 22323778, compound

HRID 1417688Notes

Reaction equation

HRID 1417688 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31](=O)[CH3:32])[CH:29]=3)[C:24]([CH3:35])([CH3:34])[CH2:23][CH:22]=2)=[CH:17][CH:16]=1>C1COCC1.CCOCC>[CH3:34][C:24]1([CH3:35])[CH2:23][CH:22]=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([CH3:14])=[CH:20][CH:19]=2)[C:30]2[CH:29]=[C:28](/[C:31](/[CH3:32])=[CH:11]/[C:12]#[N:13])[CH:27]=[CH:26][C:25]1=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 22323750HCID 22323750, compound2×

Product 1

HCID 22323778HCID 22323778, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of NaH (48.0 mg, 2.00 mmol) in THF (6 ml), was added diethylcyanomethylphosphonate (450.0 mg, 2.50 mmol). After 40 mins, a solution of 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-7-acetylnaphthalene (Compound V) 95.0 mg, (0.33 mmol) in THF (4 ml) was added. The mixture was stirred for 16 hours, diluted with ether (100 ml), and washed with water, and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure, and column chromatography (3% EtOAc/hexanes) afforded the title compound as a solid. 1H NMR (CDCl3): δ 7.39 (1H, d, J=1H), 7.32 (1H, dd, J=2.0, 8.1 Hz), 7.20-7.25 (4H, brs), 7.15 (1H, d, J=2.0 Hz), 6.03 (1H, t, J=6.0 Hz), 5.44 (1H, s), 2.42 (3H, s), 2.36 (2H, d, J=6.0 Hz), 2.35 (3H, s), 1.35 (6H, s).

Workup

  1. washwashed with water, and saturated aqueous NaCl
  2. dry with materialbefore being dried over MgSO4
  3. customRemoval of the solvents under reduced pressure, and column chromatography (3% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d8d9ba5fd41d4ac893c27ad0e152ae2d
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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