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4-(Propane-1-sulfonyl)-benzaldehyde → HCID 67276042, 화합물

HRID 1698488
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HRID 1698488 반응식
[CH2:1]([S:4]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>O1CCCC1>[CH:15]1([CH:11]([C:10]2[CH:13]=[CH:14][C:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:8][CH:9]=2)[OH:12])[CH2:17][CH2:16]1
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참가 물질

4

반응물 2

HCID 204932624-(Propane-1-sulfonyl)-benzaldehydeHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 67276042HCID 67276042, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 4-(propylsulphonyl)benzaldehyde (0.58 g) in dry tetrahydrofuran (5 mL), at −78° C. under nitrogen, was added a 0.5 M solution of cyclopropylmagnesium bromide in tetrahydrofuran (6.0 mL), slowly with stirring. The mixture was stirred for 1.75 h, quenched by addition of acetic acid (0.5 mL), then warmed to room temperature and partitioned between ethyl acetate and water. The organic phase was washed with brine, solvent stripped, and the residue chromatographed on silica gel, eluent 35% to 50% ethyl acetate in isohexane, to give the title compound as a white solid. 1H NMR (360 MHz, CDCl3) δ 7.88 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.4 Hz), 4.10 (1H, m), 3.06 (2K, m), 2.14 (1H, d, J=2.9 Hz), 1.75 (2H, m), 1.18 (1H, m), 0.99 (3H, t, J=7.4 Hz), 0.66 (2H, m), 0.49 (2H, m).

후처리

  1. stirringThe mixture was stirred for 1.75 h
  2. customquenched by addition of acetic acid (0.5 mL)
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine, solvent
  5. customthe residue chromatographed on silica gel, eluent 35% to 50% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-f7025c133fbb411f9b02b11fb7d637dc
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163956B2

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