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

HRID 846448

Reaction equation

HRID 846448 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-butylchlorodiphenylsilane (8 mL). Finally, a few mgs of 4-pyrrolidinopyridine was added as a catalyst. The reaction mixture was stirred overnight at room temperature The solution was quenched with 25% ammonium acetate and extracted with ethyl acetate, which was washed with brine (2x), 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. customwas quenched with 25% ammonium acetate
  2. extractionextracted with ethyl acetate, which
  3. washwas washed with brine (2x)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-70b674dde4cd4a08bed0f79876742ad5
Source dataset
uspto-grants-1992_08
Patent number
US05136034

Linked notes

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