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Allyl bromide → HCID 12083067, 화합물

HRID 1293102
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HRID 1293102 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[CH2:11](Br)[CH:12]=[CH2:13].[Li+].CC([N-]C(C)C)C.C(OCC)(=O)C>C1COCC1.O>[CH2:1]([C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1)[CH2:13][CH:12]=[CH2:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 40681043-Methylbenzo[d]isoxazole

생성물 1

HCID 12083067HCID 12083067, 화합물수율 103.1%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

3.0 mL dry THF was added to an oven-dried 25 mL flask and cooled to −78° C. on a dry ice/isopropanol bath. Diisopropylamine (840 μl, 6.0 mmol) was added followed by n-BuLi (3.8 mL, 1.6 M, 6.0 mmol). The LDA-solution that was obtained was left at room temperature. Compound 25 (666 mg, 5.0 mmol) was dissolved in 10 mL dry THF and added to an oven-dried 50 mL flask followed by allylbromide (476 μl, 5.5 mmol). The freshly prepared LDA-solution was slowly added at −78° C. and the mixture was left at room temperature for 30 min. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated to dryness to produce 893 mg of a light brown oil. Crude product was purified by column chromatography (heptane:ethyl acetate; 9:1; isocratic) to produce pure 26 (355 mg, 41%).

후처리

  1. waitwas left at room temperature
  2. additionadded to an oven-dried 50 mL flask
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-d041a75a3a3243edb454a424e8e5bfd1
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07238713B2

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