Tetrahydrofuran → HCID 20792908, compound

HRID 2184329Notes

Reaction equation

HRID 2184329 reaction equation
C1[CH2:5][O:4]CC1.[PH:6](=[O:12])([O-])[O:7][CH:8](C)C.[Li][CH2:14]CCC.CO[C:20](=[O:38])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([O:36][CH3:37])([O:34][CH3:35])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1>C(OCC)(=O)C>[CH3:8][O:7][P:6]([CH2:14][C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([O:36][CH3:37])([O:34][CH3:35])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1)=[O:38])(=[O:12])[O:4][CH3:5]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 20792924Methyl 3-[dimethoxy(phenyl)methyl]benzoateHCID 178418339ButyllithiumHCID 178460561HCID 178460561, compound

Product 1

HCID 20792908HCID 20792908, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a −78° C. THF solution (5 mL) of dimethylmethyl phosphonate (0.54 mL, 4.98 mmol) was added 1.6M BuLi (3.11 mL, 4.98 mmol). After stirring 40 min. a THF solution (5 mL) of 3-(dimethoxy-phenyl-methyl)-benzoic acid methyl ester (951 mg, 3.32 mmol) was added. After 15 min. the reaction mixture was warmed to room temperature. The reaction mixture was stirred an additional 1 h at room temperature and then quenched by the addition of NaHCO3 solution. Dilution with ethyl acetate was followed by washing with NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Flash chromatography (15 ethyl acetate: 1 hexanes+0.25% triethyl amine) provided {2-[3-(dimethoxy-phenyl-methyl)-phenyl]-2-oxo-ethyl}-phosphonic acid dimethyl ester (784 mg, 2.07 mmol) as an oil. Step 3

Workup

  1. customTo a −78° C
  2. additionwas added
  3. customquenched by the addition of NaHCO3 solution
  4. washby washing with NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2dcb316ba5034304b3f409b1a2412db7
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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