4-Pyrrolidinopyridine → Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

HRID 22602

Reaction equation

HRID 22602 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[C:11]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12].N1(C2C=CN=CC=2)CCCC1>C(Cl)Cl.C(N(CC)CC)C>[Si:15]([O:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[CH:2]=[O:1])([C:11]([CH3:14])([CH3:13])[CH3:12])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 755674-PyrrolidinopyridineHCID 94078tert-ButyldiphenylchlorosilaneHCID 131314553-(Hydroxymethyl)benzaldehyde

Product 1

HCID 10883279Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-hydroxymethylbenzaldehyde (step 1) (3 g) in methylene chloride (15 mL) and triethylamine (4.1 mL) was slowly added t-butylchlorodiphenyl silane (8 mL). Finally, a few mgs of 4-pyrrolidinopyridine was added as a catalyst. The reaction mixture was stirred overnight at room temperature (R.T.). The solution was quenched with 25% ammonium acetate and extracted with ethyl acetate, which was washed with brine (2×), dried over sodium sulfate, filtered and evaporated to dryness. Purification by flash chromatography, using 4% ethyl acetate in hexane afforded the title compound.

Workup

  1. customThe solution was quenched with 25% ammonium acetate
  2. extractionextracted with ethyl acetate, which
  3. washwas washed with brine (2×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1cffddb7e50e4d50a76e4abb31db29ea
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Linked notes

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