Methanol → Methyl 3-acetyladamantane-1-carboxylate

HRID 1242841ノート

反応式

HRID 1242841 の反応式
[CH3:1][Li].[CH3:3][O:4][C:5]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([C:17](Cl)=[O:18])([CH2:10]3)[CH2:8]1)[CH2:14]2)=[O:6].CO.[Cl-].[NH4+]>[Cu]I.CCOCC>[C:17]([C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([C:5]([O:4][CH3:3])=[O:6])([CH2:14]3)[CH2:8]1)[CH2:10]2)(=[O:18])[CH3:1]

参加物

7

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 541783373-Methoxycarbonyladamantane-1-carboxylic Acid ChlorideHCID 178418348HCID 178418348、化合物

生成物 1

HCID 21940569Methyl 3-acetyladamantane-1-carboxylate

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
-78 °C

実験手順

Under nitrogen, a chilled (0° C.) diethyl ether suspension of copper (I) iodide (3.0 eq) was treated with methyl lithium (6.0 eq, 1.4 M in ethyl ether). The resulting solution was chilled to −78° C. and after ten minutes a chilled (−30° C.) diethyl ether solution of 3-methoxycarbonyladamantane-1-carboxylic acid chloride was added dropwise over a five minute period. The reaction was stirred for 45 minutes at −78° C. and then quenched with MeOH (11.0 eq) and allowed to warm to room temperature. After addition of Et2O and saturated aqueous ammonium chloride solution, the mixture was stirred for ten minutes and then the organic phase was washed with saturated NH4Cl, saturated NaHCO3, brine, dried (MgSO4), filtered and concentrated to a volatile oil, which was used without further purification.

後処理

  1. temperatureUnder nitrogen, a chilled
  2. additionwas added dropwise over a five minute period
  3. temperatureto warm to room temperature
  4. stirringthe mixture was stirred for ten minutes
  5. washthe organic phase was washed with saturated NH4Cl, saturated NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a volatile oil, which
  9. customwas used without further purification

出典と根拠

ORDレコード
ord-0448677bf9ee464f9269940256cc6377
出典データセット
uspto-grants-2006_10
特許番号
US07115768B2

反応ノート

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