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Hydrochloric Acid → 1-Benzenesulfonyl-2-vinylpyrrolidine

HRID 660653
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HRID 660653 반응식
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([S:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH:25]=O)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]1([S:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH:25]=[CH2:1])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 144249041-Benzenesulfonylpyrrolidine-2-carbaldehyde

생성물 1

HCID 688399341-Benzenesulfonyl-2-vinylpyrrolidine

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028
Tetrahydrofuran
용매
2회

반응 조건

온도
-78 °C

실험 절차

To a suspension of methyl triphenylphosphonium bromide (357 mg, 1 mmol) in THF (10 mL) at −78° C. is added dropwise KHMDS (1 mmol, 2 mL of 0.5M solution). To this yellow solution is added dropwise a solution of 1-benzenesulfonylpyrrolidine-2-carbaldehyde (235 mg, 1 mmol) in THF (1 mL). The mixture is stirred at −78° C. for 2 h then is allowed to warm to RT. The mixture is poured into 1N HCl and extracted with EtOAc. The organic phase is washed with brine and dried over magnesium sulfate then the solvent removed under reduced pressure. The resulting oil is purified by flash chromatography using a gradient of 0-20% EtOAc/hexane as eluent to give the title compound.

후처리

  1. temperatureto warm to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe resulting oil is purified by flash chromatography

출처 및 근거

ORD 기록
ord-7bdd69c47f18465dbe44e7ebe1773e6f
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084448B2

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