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

HRID 626109ノート

反応式

HRID 626109 の反応式
[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

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 86642922HCID 86642922、化合物HCID 178461630HCID 178461630、化合物

生成物 1

HCID 510398611-(4-Hydroxycyclohexyl)propan-1-one収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9f37ee00452a44258c65951390588349
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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