Tetrahydrofuran → HCID 86756620, compound

HRID 324233Notes

Reaction equation

HRID 324233 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(=O)C)[CH:29]=3)[C:24]([CH3:35])([CH3:34])[CH2:23][CH:22]=2)=[CH:17][CH:16]=1.[CH2:36]1COC[CH2:37]1>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:11](=[CH:36][CH3:37])[C:12]#[N:13])[CH:27]=[CH:26][C:25]1=2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 22323750HCID 22323750, compound2×

Product 1

HCID 86756620HCID 86756620, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. 1 H 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-cfbec7d54a4e40a4a8a12df3fbf896c0
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

Loading…