Benzyl 4-formylbenzoate → HCID 57925927, compound

HRID 1013481Notes

Reaction equation

HRID 1013481 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:19]([O-:24])([O:22][CH3:23])[O:20][CH3:21]>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:18])[C:10]1[CH:11]=[CH:12][C:13]([CH:16]([P:19]([O:22][CH3:23])([O:20][CH3:21])=[O:24])[OH:17])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11528845Benzyl 4-formylbenzoateHCID 21884954Dimethylphosphite

Product 1

HCID 57925927HCID 57925927, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-formyl-benzoic acid benzyl ester (0.50 g, 2.08 mmol) in THF (2.0 mL) was cooled to 0° C., then dimethyl phosphite (0.25 g, 2.29 mmol) and N,N,N′M′-tetramethyl-guanidine (0.02 g, 0.21 mmol) was added dropwise. The reaction mixture was warmed to ambient temperature. After stirring for 45 mins the reaction mixture was diluted with EtOAc and washed with 1N aqueous HCl (2×), brine, then dried (MgSO4) and concentrated in vacuo to give the title compound: MS: cal'd 351 (MH+), exp 351 (MH+)

Workup

  1. washwashed with 1N aqueous HCl (2×), brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb628ef23e384835835f26195091572d
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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