Ethyl Acetate → 1-(4-Hydroxycyclohexyl)propan-1-one

HRID 626109노트

반응식

HRID 626109 반응식
[CH3:1][CH2:2][Mg+].[Br-].[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](N(OC)C)=[O:13])[CH2:8][CH2:7]1.CCOC(C)=O>C1COCC1>[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:13])[CH2:2][CH3:1])[CH2:8][CH2:7]1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 86642922HCID 86642922, 화합물HCID 178461630HCID 178461630, 화합물

생성물 1

HCID 510398611-(4-Hydroxycyclohexyl)propan-1-one수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

EtMgBr (1 M, 3.0 eq, 20 mL) was added to a solution of 4-hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (1.0 g, 1.0 eq) in dry THF at 0° C. Once addition was complete, the mixture was stirred overnight. The reaction mixture was washed with saturated NH4Cl (aq), and extracted by EtOAc. The extract was dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc=1:1 to give the desired product (0.6 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ 3.50-3.64 (m, 1H), 2.47 (q, J=7.2 Hz, 2H), 2.28-2.37 (m, 1H), 2.00-2.10 (m, 2H), 1.88-1.94 (m, 2H), 1.70-1.80 (m, 1H), 1.21-1.49 (m, 4H), 1.05 (t, J=7.2 Hz, 3H).

후처리

  1. additionOnce addition
  2. washThe reaction mixture was washed with saturated NH4Cl (aq)
  3. extractionextracted by EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography with petroleum ether

출처 및 근거

ORD 기록
ord-9f37ee00452a44258c65951390588349
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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