Hydrochloric Acid → 3-(2,4-Bis{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)-4-methyl-7-{[2-(trimethylsilyl)ethoxy]methoxy}-2H-1-benzopyran-2-one

HRID 2214302Notes

Reaction equation

HRID 2214302 reaction equation
Cl.[CH3:2][Si:3]([CH3:47])([CH3:46])[CH2:4][CH2:5][O:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:12]=[CH:11][C:10]=1[C:24]1[C:25](=[O:45])[O:26][C:27]2[C:32]([C:33]=1[CH2:34]Br)=[CH:31][CH:30]=[C:29]([O:36][CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:28]=2>CCOC(C)=O>[CH3:46][Si:3]([CH3:2])([CH3:47])[CH2:4][CH2:5][O:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[CH:12]=[CH:11][C:10]=1[C:24]1[C:25](=[O:45])[O:26][C:27]2[C:32]([C:33]=1[CH3:34])=[CH:31][CH:30]=[C:29]([O:36][CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:28]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219591903-(2,4-Bis{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)-4-(bromomethyl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-2H-1-benzopyran-2-one

Product 1

HCID 219592253-(2,4-Bis{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)-4-methyl-7-{[2-(trimethylsilyl)ethoxy]methoxy}-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into 1N HCl (10 mL) (1N HCl solution made using concentrated HCl in 1:1 THF:IPA) was dissolved 3-[2,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4-bromomethyl-7-(2-trimethylsilanyl-ethoxymethoxy)-chromen-2-one (200 mg, 0.544 mmol) and the resulting mixture was stirred for 24 h at room temperature. The reaction mixture was then diluted with EtOAc (100 mL) and the organic layer washed with water (2×20 mL) and brine (30 mL). The organic layer was dried over Na2SO4, filtered and the organic solvent evaporated to yield the title compound, 3-[2,4-Bis-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-chromen-2-one as a crude solid.

Workup

  1. washthe organic layer washed with water (2×20 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe organic solvent evaporated

Sources & evidence

ORD record
ord-14aff3a65f5f41caa0088c67fccba332
Source dataset
uspto-grants-2006_09
Patent number
US07105679B2

Reaction notes

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