Ethyl Acetate → {4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl Ester

HRID 2378837Notes

Reaction equation

HRID 2378837 reaction equation
[C:1]1([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]2[C:22]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[C:23]3[C:27](=[C:28]([CH3:32])[C:29]=2[O:30][CH3:31])[CH2:26][O:25][C:24]3=[O:33])(=[O:16])[O:9]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CCOC(C)=O>C1COCC1>[C:1]1([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]2[C:22]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:38])[CH3:39])=[C:23]3[C:27](=[C:28]([CH3:32])[C:29]=2[O:30][CH3:31])[CH2:26][O:25][C:24]3=[O:33])(=[O:9])[OH:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 76546201{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Diphenyl Ester

Product 1

HCID 76548829{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl EsterYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic acid diphenyl ester (75 mg, 0.126 mmol) in THF (5 mL) was added 1N NaOH (0.1 mL) solution. The mixture was allowed to stir at room temperature for 16 hours. EtOAc was added and the resulting mixture was washed with 1H HCl. The organic layer was concentrated to dryness and the residue was purified by RP HPLC using a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, 0.1% TFA to provide 24.8 mg (38%) of the desired product. MS (m/z) 517 [M−H]−, 541 [M+Na]+.

Workup

  1. washthe resulting mixture was washed with 1H HCl
  2. concentrationThe organic layer was concentrated to dryness
  3. customthe residue was purified by RP HPLC

Sources & evidence

ORD record
ord-642c171d937649a5a5fa1d49d6648ee2
Source dataset
uspto-grants-2008_12
Patent number
US07470724B2

Reaction notes

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