2,3-Diisopropoxy-4-methoxybenzaldehyde → 2,3-Diisopropoxy-1-(1-hydroxyethyl)-4-methoxybenzene

HRID 9309

반응식

HRID 9309 반응식
[CH:1]([O:4][C:5]1[C:12]([O:13][CH:14]([CH3:16])[CH3:15])=[C:11]([O:17][CH3:18])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:3])[CH3:2].[CH3:19][Li]>C(OCC)C>[CH:1]([O:4][C:5]1[C:12]([O:13][CH:14]([CH3:16])[CH3:15])=[C:11]([O:17][CH3:18])[CH:10]=[CH:9][C:6]=1[CH:7]([OH:8])[CH3:19])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 219865542,3-Diisopropoxy-4-methoxybenzaldehydeHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 219865522,3-Diisopropoxy-1-(1-hydroxyethyl)-4-methoxybenzene수율 84%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 22 (23.10 g, 91.56 mmol) in dry ethyl ether (150 mL) was added dropwise methyllithium (98.10 mL, 1.4 M in EtO2, 1.37.3 mmol) at 0° C. under nitrogen. The reaction mixture was stirred for 2 h allowing too reach room temperature. The reaction was slowly quenched with water, the phases were separated, and the aqueous phase was extracted with ethyl ether (3×150 mL). The combined organic solutions were dried over MgSO4 and concentrated over reduced pressure. Purification by flash column chromatography (silica gel, elution with hexanes/EtOAc: 80/20) provided the protected alcohol 20.62 g (76.77 mmol, 84%) as a pale yellow oil.

후처리

  1. customallowing too reach room temperature
  2. customThe reaction was slowly quenched with water
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl ether (3×150 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated over reduced pressure
  7. customPurification
  8. washby flash column chromatography (silica gel, elution with hexanes/EtOAc: 80/20)

출처 및 근거

ORD 기록
ord-984178fe26d140788905778d11aa6935
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091240B2

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