Tetrahydrofuran → Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

HRID 1404719

반응식

HRID 1404719 반응식
[Li].[CH3:2][C:3]([O-:6])(C)C.C[C:8]([O-:11])(C)C.CC([O-])(C)C.[Al+3].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>S(=O)(=O)(O)[O-].[Na+]>[OH:18][CH2:22][C:21]1([C:8]([O:6][CH2:3][CH3:2])=[O:11])[CH2:19][CH2:20]1

참가 물질

4

반응물 2

HCID 8028Tetrahydrofuran2회HCID 6328594Aluminium lithium tri-tert-butoxide hydride

생성물 1

HCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate수율 88%

시약·촉매·용매 1

HCID 516919Sodium Bisulfate용매

반응 조건

온도
65 °C

실험 절차

A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (12 mL, 12 mmol, 2.2 equiv) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (1.0 mL, 5.7 mmol, 1.0 equiv) in tetrahydrofuran (19 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (100 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layers were dried (MgSO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a pale yellow oil (850 mg, 88%): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H).

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (4×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationgravity-filtered
  5. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-8ba806daee914729ad7082735ad051d3
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912338B2

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