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Tributyltin Chloride → HCID 71143891, 화합물

HRID 2173040
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HRID 2173040 반응식
I[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[CH2:8][CH2:7][O:6][CH2:5]2.C([Li])CCC.[CH2:16]([Sn:20]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])Cl)[CH2:17][CH2:18][CH3:19]>C1COCC1>[CH2:26]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[CH2:8][CH2:7][O:6][CH2:5]2)[CH2:27][CH2:28][CH3:29]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 66914783HCID 66914783, 화합물HCID 178418339Butyllithium

생성물 1

HCID 71143891HCID 71143891, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a cold (−78° C.) mixture of 7-iodo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine (300 mg, 1.205 mmol) and THF (10 mL) was added n-butyllithium (0.530 mL, 1.325 mmol) dropwise under a nitrogen atmosphere. The reaction mixture was stirred at −78° C. for 60 minutes, after which tributylchlorostannane (0.392 mL, 1.445 mmol) was added. The reaction mixture was stirred at −78° C. 60 minutes, then warmed to room temperature and stirred for 1 hour. The reaction was quenched with brine (10 mL) and extracted with EtOAc (2×25 mL). The organic phase was separated, dried over sodium sulfate, concentrated, and purified via flash column chromatography to give the title compound as an oil, which was used without further purification (300 mg, 60%).

후처리

  1. stirringThe reaction mixture was stirred at −78° C
  2. temperature60 minutes, then warmed to room temperature
  3. stirringstirred for 1 hour
  4. customThe reaction was quenched with brine (10 mL)
  5. extractionextracted with EtOAc (2×25 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified via flash column chromatography

출처 및 근거

ORD 기록
ord-f4cbdfed318d426c96ed76e62eea3b06
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056873B2

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