Lithium Hexamethyldisilazide → methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate

HRID 1377749Notes

Reaction equation

HRID 1377749 reaction equation
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])[CH3:3].[CH3:12][Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:22]1([O:27][C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])C=O)[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH3:12][O:6][C:4](=[O:5])/[CH:2]=[CH:3]/[C:30]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:28]([O:27][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:29]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 5702848methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trimethylphosphonoacetate (13 mL, 82 mmol) in 36 mL of THF at 0° C. was added lithium bis(trimethylsilyl)amide (82 mL of 1M THF solution, 82 mmol). This solution was stirred for 20 min, and a solution of 3-cyclopentoxy-4-methoxybenzaldehyde (15 g, 68 mmol) in 30 mL of THF was then added dropwise via addition funnel. When reaction was judged complete by TLC analysis, the reaction was diluted with ethyl acetate:hexanes (1:1), and the organic layer was washed with H2O and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to afford (E)-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-en-oate as a pale yellow solid (17.2 g, 92%). 1H-NMR (300 MHz): δ 3.79 (s, 3), 3.86 (s, 3), 6.28 (d, 1, J=16), 7.52 (d, 1, J=16).

Workup

  1. customWhen reaction
  2. washthe organic layer was washed with H2O and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f5a32e51757451c82cec3f701473e82
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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