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

HRID 846448

반응식

HRID 846448 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-70b674dde4cd4a08bed0f79876742ad5
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05136034

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