Potassium Carbonate → 4-Ethyl-2-[2-(1,1-dimethylethyldimethylsilyloxy)-ethoxy]benzaldehyde

HRID 355274

Reaction equation

HRID 355274 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:10]=[O:11])=[C:7]([OH:9])[CH:8]=1)[CH3:2].[CH3:12][C:13]([Si:16]([CH3:22])([CH3:21])[O:17][CH2:18][CH2:19]Br)([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:10]=[O:11])=[C:7]([O:9][CH2:19][CH2:18][O:17][Si:16]([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:22])[CH3:21])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 102360174-Ethyl-2-hydroxybenzaldehyde

Product 1

HCID 189415974-Ethyl-2-[2-(1,1-dimethylethyldimethylsilyloxy)-ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to that of Step (b) of Example 1, using 17.0 grams (0.113 mole) of 5-ethyl-2-formylphenol, 27.7 grams (0.116 mole) of 2-(1,1-dimethylethyldimethylsilyloxy)ethyl bromide, 19.2 grams (0.139 mole) of potassium carbonate, and a catalytic amount of 18-crown-6 in 200 mL of THF. The yield of the subject compound was 12.7 grams, following purification by column chromatography on silica gel. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step (b) of Example 1
  2. custompurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0fbdafd837e44cd8d95fec8f23caaa1
Source dataset
uspto-grants-1998_11
Patent number
USH0001759

Linked notes

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