Lithium diisopropylamide → 2-Ethoxy4-methyl-4-phenylhex-2-enoic acid ethyl ester

HRID 2106046Notes

Reaction equation

HRID 2106046 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][CH2:7][CH2:8]P(OCC)(OCC)=O)[CH3:2].[Li+].CC([N-]C(C)C)C.[CH3:26][C:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH2:30][CH3:31])[CH:28]=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:6][CH2:7][CH3:8])=[CH:28][C:27]([CH3:26])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:30][CH3:31])[CH3:2]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 127656012-Methyl-2-phenylbutanalHCID 15729465Ethyl (diethoxyphosphoryl)ethoxyacetate

Product 1

HCID 690552152-Ethoxy4-methyl-4-phenylhex-2-enoic acid ethyl esterYield 116%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (0° C.) solution of 7.4 g of (diethoxyphosphoryl)ethoxy acetic acid ethyl ester in 30 mL of THF was added 16 mL of a 1.8M solution of LDA. After 30 minutes, 4.2 g of 2-methyl-2-phenylbutyraldehyde in 30 mL of THF was added dropwise by syringe. The mixture was warmed to room temperature, quenched with saturated aqueous ammonium chloride, and extracted with diethyl ether. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to afford 8.3 g of 2-ethoxy4-methyl-4-phenylhex-2-enoic acid ethyl ester as an orange oil and a mixture of geometric isomers (2:1).

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47c8fbddd95e478083200a37c728d39c
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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