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Dimethylformamide → (1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-carbaldehyde

HRID 2056758
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HRID 2056758 반응식
[Si:1]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29](Br)=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:39]=[O:40]>C1COCC1>[Si:1]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH:39]=[O:40])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

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HCID 6228DimethylformamideHCID 693073122-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethyl tert-butyl(diphenyl)silyl etherHCID 178418339Butyllithium

생성물 1

HCID 86596016(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a stirred solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethyl tert-butyl(diphenyl)silyl ether (2.5 g, 5.05 mmol) in dry THF (60 mL), cooled to −78° C. under nitrogen, was slowly added n-butyllithium (2.5M in THF) (5.4 mL, 13.5 mmol). After 30 min stirring at −78° C., dry dimethylformamide (3.5 mL, 45 mmol) was added and the reaction allowed to warm to room temperature overnight. The reaction was quenched by addition of water and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The resultant yellow oil was purified by flash chromatography on silica, eluting with ethyl acetate/hexane (0:4 to 1:3), to yield the title compound as a colourless oil.

후처리

  1. temperatureto warm to room temperature overnight
  2. customThe reaction was quenched by addition of water
  3. extractionextracted into ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resultant yellow oil was purified by flash chromatography on silica
  9. washeluting with ethyl acetate/hexane (0:4 to 1:3)

출처 및 근거

ORD 기록
ord-dee50f8e298343cb8e5f5d6f87e2daca
출처 데이터셋
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07335660B2

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