Hydrochloric Acid → Diethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl2-naphthyl)-1-ethenyl]-benzenephosphonate

HRID 2073602Notes

Reaction equation

HRID 2073602 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19])=[CH:12][CH:11]=1)(OCC)=O)C.[H-].[Na+].[CH:26]([C:28]1[CH:37]=[CH:36][C:35]2[C:34]([CH3:39])([CH3:38])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]=2[CH:29]=1)=O.Cl>CS(C)=O>[CH3:38][C:34]1([CH3:39])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]2[CH:29]=[C:28](/[CH:26]=[CH:9]/[C:10]3[CH:11]=[CH:12][C:13]([P:16]([O:17][CH2:18][CH3:19])(=[O:20])[O:21][CH2:22][CH3:23])=[CH:14][CH:15]=3)[CH:37]=[CH:36][C:35]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 104208875,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehydeHCID 19857614Diethyl 4diethylphosphonomethylbenzenephosphonate

Product 1

HCID 14371701Diethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl2-naphthyl)-1-ethenyl]-benzenephosphonateYield 32.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

A solution of 22 g (53 millimoles) of diethyl 4diethylphosphonomethylbenzenephosphonate in 100 ml of dimethyl sulfoxide was added dropwise to a suspension of 1.8 g (64 millimoles) of sodium hydride in 50 ml of dry dimethyl sulfoxide at room temperature. Stirring was continued for 1 hour, after which a solution of 8.7 g (40 millimoles) of 2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene in 75 ml of dimethyl sulfoxide was added dropwise. Stirring was continued for 16 hours at room temperature and the mixture was poured onto water, acidified with 2N hydrochloric acid and extracted three times with ether. The combined organic phases were washed twice with water and twice with saturated sodium chloride solution, dried over sodium sulfate and evaporated down. The residue was purified by column chromatography (silica gel; heptane/0.55 - 10% ethyl acetate) to give 5.5 g of the title compound of melting point 83°-84° C.

Workup

  1. stirringStirring
  2. waitwas continued for 16 hours at room temperature
  3. additionthe mixture was poured onto water
  4. extractionextracted three times with ether
  5. washThe combined organic phases were washed twice with water and twice with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated down
  8. customThe residue was purified by column chromatography (silica gel; heptane/0.55 - 10% ethyl acetate)

Sources & evidence

ORD record
ord-98588f0719b248a09e5a0e3597845832
Source dataset
uspto-grants-1990_04
Patent number
US04918212

Reaction notes

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