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Water → 4-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butan-1-ol

HRID 1047488
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인쇄 미리보기

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HRID 1047488 반응식
C[O:2][C:3](=O)[CH2:4][CH:5]([CH3:26])[CH:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=1[F:15].[BH4-].[Li+].O.C(OCC)(=O)C>C1COCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([CH:6]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=2[F:15])[CH:5]([CH3:26])[CH2:4][CH2:3][OH:2])(=[O:17])=[O:18])=[CH:24][CH:23]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 589501144-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butyric acid methyl ester

생성물 1

HCID 589506574-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butan-1-ol

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

4-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butyric acid methyl ester (0.79 g, 1.88 mmol) was dissolved in 10 mL of THF and lithium borohydride (0.5 g, excess) was added. The reaction mixture was stirred at room temperature overnight. 50 mL of water and 50 mL of EtOAc were added. The organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated. The residue was used in next step without further purification (0.71 g, 96%). 1H NMR (CDCl3 400 MHz) δ 7.61 (m, 2H), 7.36 (m, 2H), 7.06 (m, 1H), 6.82 (m, 0.5H), 6.60 (m, 0.5H), 4.79 (m, 0.5H), 4.56 (m, 0.5H), 3.85 (m, 1H), 3.68 (m, 1H), 3.12 (m, 1H), 2.39 (m, 0.5H), 1.95 (m, 0.5H), 1.57 (m, 0.5H), 1.46 (dd, J=4.4 and 5.9 Hz, 1.5H), 1.32 (m, 0.5H), 0.92 (dd, J=7.3 and 9.5 Hz, 1.5H).

후처리

  1. washThe organic layer was washed with brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was used in next step without further purification (0.71 g, 96%)

출처 및 근거

ORD 기록
ord-9ae5a6e824fd4ecba5eaa114a504dee0
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569521B2

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