1-Bromo-4-chlorobutane → t-Butyl 1-(4-chlorobutyl)-1-cyclopropanecarboxylate

HRID 239039노트

반응식

HRID 239039 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.C1(C(OC(C)(C)C)=O)CC1.BrCCCC[Cl:31].[Li+].CC([N-]C(C)C)C>>[Cl:31][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1

참가 물질

5

반응물 4

HCID 813641-Bromo-4-chlorobutaneHCID 2724682Lithium diisopropylamideHCID 13676038tert-Butyl cyclopropanecarboxylateHCID 21932036Tert-Butyl 1-(4-bromobutyl)cyclopropanecarboxylate

생성물 1

HCID 21932032t-Butyl 1-(4-chlorobutyl)-1-cyclopropanecarboxylate

실험 절차

Compound 104a was prepared, likewise the procedure described for 103b, starting from t-butyl cyclopropanecarboxylate (Kohlrausch, K. W. F. et al. Z Elektrochem. Angew. Phys. Chem, 1937, 43, 282-285) (12.5 g, 88 mmol), 1-bromo-4-chlorobutane (13.7 mL, 117 mmol) and LDA (prepared from BuLi (2.5M in hexanes, 37 mL, 92.5 mmol) and iPr2NH (12.3 mL, 88 mmol, distilled from NaOH)) to give, after purification by fractional distillation under reduced pressure, 104a (10.73 g 52%) as a colorless oil. bp: T=57-61° C. (p=0.001 mbar). 1H NMR: δ 3.52 (t, J=6.6 Hz, 2H), 1.76 (quintet, J=6.8 Hz, 2H), 1.64-1.54 (m, 2H), 1.51-1.46 (m, 2H), 1.42 (s, 9H), 1.12 (dd, J=6.6, 3.9 Hz, 2H), 0.60 (dd, J=6.6, 3.9 Hz, 2H). 13C NMR: δ 173.9, 80.0, 45.1, 33.6, 32.9, 28.2 (3×), 25.3, 24.2, 15.4 (2×). HRMS calcd for C12H22ClO2 (MH+): 233.1308, found: 233.1308.

후처리

  1. customto give
  2. customafter purification
  3. distillationby fractional distillation under reduced pressure, 104a (10.73 g 52%) as a colorless oil
  4. customT=57-61° C. (p=0.001 mbar)

출처 및 근거

ORD 기록
ord-866fdd971e574bd28b86e9cdf0c7a400
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642653B2

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