Methyl iodide → HCID 12723453、化合物

HRID 1871757ノート

反応式

HRID 1871757 の反応式
[H-].[Na+].[CH:3]1([OH:10])[CH2:8][CH2:7]C(O)C=C1.[CH3:11]I.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH3:15][O:16][CH:17]1[CH2:13][CH2:14][CH:3]([O:10][CH3:11])[CH:8]=[CH:7]1

参加物

5

反応物 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5508252-Cyclohexene-1,4-diol

生成物 1

HCID 12723453HCID 12723453、化合物収率 91%

実験手順

Lit., J. Org. Chem., 53:5695 (1988). To 14.3 g (328 mmol) sodium hydride (55% dispersion in oil) was added dropwise at 0° C. with stirring a solution of 10.1 g (88.5 mmol) (1RS,4RS)-cyclohex-2-ene-1,4-diol in 100 ml THF. 34 ml (546 mmol) methyl iodide was then added and stirring continued for an additional 48 h at room temperature. The reaction was quenched with saturated ammonium chloride solution and extracted with ether. The combined organic extracts were washed successively with saturated ammonium chloride solution and saturated brine, dried over sodium sulphate, and concentrated in vacuo to afford 11.5 g (91%) of the title compound as a yellow oil. 1H NMR d (250 MHz, CDCl3) 5.90 (2H, s), 3.82 (2H, br t), 3.37 (6H, s), 2.10 (2H, m), 1.51 (2H, m).

後処理

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed successively with saturated ammonium chloride solution and saturated brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d6c19cbcbcbb43eebe26dbccc10d2342
出典データセット
uspto-grants-2000_08
特許番号
US06103910

反応ノート

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