HCID 21959306, compound → HCID 21959134, compound

HRID 2214309Notes

Reaction equation

HRID 2214309 reaction equation
C[Si](C)(C)CCOC[O:7][C:8]1[CH:13]=[C:12]([O:14]COCC[Si](C)(C)C)[CH:11]=[CH:10][C:9]=1[C:23]1[C:24](=[O:47])[O:25][C:26]2[C:31]([C:32]=1[CH2:33][C:34](=[O:37])[CH2:35][Cl:36])=[CH:30][CH:29]=[C:28]([O:38]COCC[Si](C)(C)C)[CH:27]=2>Cl.C(OCC)(=O)C>[Cl:36][CH2:35][C:34](=[O:37])[CH2:33][C:32]1[C:31]2[C:26](=[CH:27][C:28]([OH:38])=[CH:29][CH:30]=2)[O:25][C:24](=[O:47])[C:23]=1[C:9]1[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=1[OH:7]

Participants

4

Reactant 1

HCID 21959306HCID 21959306, compound

Product 1

HCID 21959134HCID 21959134, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[2,4-Bis-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4-(3-chloro-2-oxo-propyl)-7-(2-trimethylsilanyl-ethoxymethoxy)-chromen-2-one (0.846 g, 1.13 mmol) in HCl (1N, 40 mL 1:1 THF:iPrOH) was stirred overnight at 25° C. The reaction mixture was then diluted with ethyl acetate (10 mL) and washed with brine (2×30 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The organic layers were combined, dried, concentrated and purified by silica gel column chromatograph (5% MeOH/DCM) to yield the title compound as white crystals.

Workup

  1. washwashed with brine (2×30 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatograph (5% MeOH/DCM)

Sources & evidence

ORD record
ord-9592c42d3973499c9c826df2cddaaf63
Source dataset
uspto-grants-2006_09
Patent number
US07105679B2

Reaction notes

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