Trimethyl phosphonoacetate → HCID 178443560, compound

HRID 650847Notes

Reaction equation

HRID 650847 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]([CH2:10]P(OC)(OC)=O)=[O:9].[CH2:17]([C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][O:31][C:32]2[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=2)[CH2:26][CH2:25]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O1CCCC1>[CH2:17]([C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][O:31][C:32]2[CH:33]=[CH:34][C:35]([CH:36]=[CH:10][C:8]([O:7][CH3:6])=[O:9])=[CH:38][CH:39]=2)[CH2:26][CH2:25]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 178418339ButyllithiumHCID 178443561HCID 178443561, compound

Product 1

HCID 178443560HCID 178443560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

27.6 ml of a 1.6 N butyllithium solution are added dropwise to a solution of 6.4 ml of trimethyl phosphonoacetate in 50 ml of dry tetrahydrofuran at 0° C. in the course of 10 minutes. Stirring is carried out for 1.5 hours at 0° C. and a solution of 10.3 g of crude 4-[(trans-4-heptylcyclohexyl)methoxy]benzaldehyde in 50 ml of dry tetrahydrofuran is then added dropwise in the course of 5 minutes at the same temperature. The mixture is then slowly warmed up to room temperature and is allowed to react for 15 hours. The reaction mixture is then partitioned between methylene chloride and 1 N hydrochloric acid and the organic phase is washed with saturated sodium bicarbonate solution and water, dried over magnesium sulfate and evaporated down. Chromatography over silica gel using ethyl acetate/hexane (1:9) and subsequent repeated crystallization from hexane/ethyl acetate give methyl 4-[(trans-4-heptylcyclohexyl)methoxy]cinnamate.

Workup

  1. customto react for 15 hours
  2. customThe reaction mixture is then partitioned between methylene chloride and 1 N hydrochloric acid
  3. washthe organic phase is washed with saturated sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. customcrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4ab16b0d4a3b4e5aa3be77648b98342e
Source dataset
uspto-grants-2001_08
Patent number
US06277502B1

Reaction notes

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