HCID 22323774, compound → HCID 86586185, compound

HRID 1955556Notes

Reaction equation

HRID 1955556 reaction equation
C([C:3]([CH2:16][CH3:17])(P(=O)([O-])[O-])/[C:4](/[CH3:11])=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C([Li])CCC.[CH3:23][C:24]1([CH3:46])[CH2:33][CH:32]=[C:31]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)[C:30]2[CH:29]=[C:28](/[C:41](/C)=[CH:42]/C=O)[CH:27]=[CH:26][C:25]1=2>C1COCC1.CCOCC>[CH3:11]/[C:4](/[CH:3]=[CH:16]/[CH:17]=[C:41](/[C:28]1[CH:27]=[CH:26][C:25]2[C:24]([CH3:23])([CH3:46])[CH2:33][CH:32]=[C:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[C:30]=2[CH:29]=1)\[CH3:42])=[CH:5]\[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 22323774HCID 22323774, compoundHCID 131720750HCID 131720750, compoundHCID 178418339Butyllithium

Product 1

HCID 86586185HCID 86586185, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (-78° C.) solution of diethyl-(E)-3-ethoxycarbonyl-2-methylallylphosphonate [prepared in accordance with J. Org. Chem. 39: 821 (1974)] 264.0 mg, (1.00 mmol) in THF (2 ml) was added 26.0 mg (0.41 mmol, 0.65 ml)of n-butyllithium in hexanes (1.6M solution) followed immediately by the addition of (E)-3-(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalen-yl)-2-butenal (Compound X) 82.0 mg, 0.26 mmol) in THF (3 ml). After 1 hour, the reaction mixture was diluted with ether (60 ml), washed with water (5 ml), saturated aqueous NaCl (5 ml) and dried over MgSO4. After removal of the solvents under reduced pressure, the title compound was isolated as an oil by column chromatography (5% EtOAc/hexanes, followed by HPLC using 1% EtOAc/hexanes). 1H NMR (acetone-d6): δ 7.36-7.43 (2H, m), 7.18-7.27 (4H, m), 7.17 (1H, d, J=1.7 Hz), 7.08 (1H, dd, J=11.2, 15.2 Hz), 6.46 (1H, d, J=11.2 Hz), 6.38 (1H, d, J=15.2 Hz), 5.98 (1H, t, J=4.7 Hz), 5.78 (1H, s), 4.10 (2H, q, J=7.1 Hz), 2.35 (3H, s), 2.33 (3H, s), 2.32 (2H, d, J=4.7 Hz), 2.12 (3H, s), 1.31 (6H, s), 1.22 (3H, t, J=7.1 Hz).

Workup

  1. washwashed with water (5 ml), saturated aqueous NaCl (5 ml)
  2. dry with materialdried over MgSO4
  3. customAfter removal of the solvents under reduced pressure

Sources & evidence

ORD record
ord-6094ed8efdaa4e2aadcd16ebbbcc0b22
Source dataset
uspto-grants-1998_07
Patent number
US05776699

Reaction notes

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