Benzaldehyde, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]- → HCID 66648906, compound

HRID 1774402Notes

Reaction equation

HRID 1774402 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23](C=O)=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2(C3C=CC=CC=3)CCP(C3C=CC=CC=3)[C:35]2=[CH:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])C=CC=CC=1>C1C=CC=CC=1.CCCCCC.C(OCC)C.C(O)(=O)C1C=CC=CC=1>[Si:1]([O:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23](/[CH:35]=[CH:45]/[C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 11406203Benzaldehyde, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-HCID 73993302HCID 73993302, compound

Product 1

HCID 66648906HCID 66648906, compoundYield 347.8%

Reagents, catalysts & solvents 4

HCID 243Benzoic AcidCatalystHCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-(t-butyldiphenylsilyloxymethyl)benzaldehyde (3.26 g, 8.71 mmol) in benzene (80 mL) were added ethyl (triphenylphospholanylidene)acetate (3.19 g, 9.14 mmol) and benzoic acid (116.0 mg, 0.950 mmol) at room temperature, and the mixture was heated under reflux with stirring for 2 h. The reaction mixture was directly concentrated under reduced pressure, and the residue thus obtained was diluted with hexane (80 mL) and diethyl ether (40 mL) and stirred for 8 h. Precipitated solids were filtered, and the residue obtained by concentrating the filtrate under reduced pressure was subjected to silica gel column chromatography (hexane-ethyl acetate 25:1) to give 13.47 g of ethyl (E)-3-{4-[(t-butyldiphenylsilyloxy)methyl]phenyl}acrylate as oil (yield: 90%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was directly concentrated under reduced pressure
  4. customthe residue thus obtained
  5. stirringstirred for 8 h
  6. customPrecipitated solids
  7. filtrationwere filtered
  8. customthe residue obtained
  9. concentrationby concentrating the filtrate under reduced pressure

Sources & evidence

ORD record
ord-e2b348633ae241ae9cf430756a4c6374
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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