Trimethyl phosphonoacetate → HCID 178445600, compound

HRID 1739500Notes

Reaction equation

HRID 1739500 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]([CH2:10]P(OC)(OC)=O)=[O:9].[CH2:17]([C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[CH2:18][CH:19]=[CH2:20]>O1CCCC1>[CH2:17]([C@H:21]1[CH2:22][CH2:23][C@H:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36](/[CH:39]=[CH:10]/[C:8]([O:7][CH3:6])=[O:9])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:25][CH2:26]1)[CH2:18][CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 178418339ButyllithiumHCID 178445601HCID 178445601, compound

Product 1

HCID 178445600HCID 178445600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

27.6 ml of a 1.6N butyllithium solution were added dropwise at 0° C. within 10 minutes to a solution of 6.4 ml of trimethyl phosphonoacetate in 50 ml of dry tetrahydrofuran. The mixture was stirred at 0° C. for 1.5 hours and thereafter a solution of 11.5 g of crude trans-4'-[4-(3-butenyl)cyclohexyl]biphenyl-4-carboxaldehyde in 50 ml of dry tetrahydrofuran was added dropwise within 5 minutes at the same temperature. Subsequently, the mixture was warmed slowly to room temperature and left to react for 15 hours. The reaction mixture was then partitioned between methylene chloride and 1N hydrochloric acid and the organic phase was washed with saturated sodium bicarbonate solution and water, dried over magnesium sulphate and evaporated. Chromatography on silica gel with ethyl acetate/hexane (1:9) and subsequent repeated recrystallization from hexane/ethyl acetate gave methyl trans-(E)-3-{4'-[4-(3-butenyl)cyclohexyl]biphenyl-4-yl}acrylate.

Workup

  1. temperatureSubsequently, the mixture was warmed slowly to room temperature
  2. waitleft
  3. customto react for 15 hours
  4. customThe reaction mixture was then partitioned between methylene chloride and 1N hydrochloric acid
  5. washthe organic phase was washed with saturated sodium bicarbonate solution and water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customrecrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ec0c2f90169a4f12b1a6f88e76e7c20f
Source dataset
uspto-grants-1999_10
Patent number
US05965761

Reaction notes

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