HCID 22323774, compound → HCID 86586185, compound

HRID 324234Notes

Reaction equation

HRID 324234 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-ethoxycabonyl-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 (1.6 M 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-44ddd840e42b4d6e93075d6ec3e05f20
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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