Methanol → Methyl 3-acetyladamantane-1-carboxylate

HRID 1242841노트

반응식

HRID 1242841 반응식
[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]

참가 물질

7

반응물 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 541783373-Methoxycarbonyladamantane-1-carboxylic Acid ChlorideHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 21940569Methyl 3-acetyladamantane-1-carboxylate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3283Diethyl Ether용매3회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0448677bf9ee464f9269940256cc6377
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115768B2

반응 노트

불러오는 중…