Diethyl Ether → HCID 57577374, 화합물

HRID 1921692노트

반응식

HRID 1921692 반응식
[CH2:1]([O:3][C:4](=[O:34])[C:5]([NH:30][C:31](=[O:33])[CH3:32])([CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=2)[CH:12]1O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(OCC)C>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4](=[O:34])[C:5]([NH:30][C:31](=[O:33])[CH3:32])([C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=2)[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

참가 물질

4

반응물 2

HCID 3283Diethyl EtherHCID 57577369HCID 57577369, 화합물2회

생성물 1

HCID 57577374HCID 57577374, 화합물수율 63.3%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
0 °C

실험 절차

2-Acetylamino-2-(6-octyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester (compound A, 755 mg, 1.58 mmol)) is dissolved in acetic anhydride (5 mL) followed at 0° C. by a catalytic amount of ferric chloride (66 mg, 0.4 mmol). The reaction is stirred at 0° C. for an additional 2 hours, and 20 mL of diethyl ether is added. The reaction is carefully poured into 50 mL of ice cold water and the organic layer quickly separated. The organic layer is re-extracted with methylene chloride (2×20 mL) and the combined organic layers were washed once with brine (20 mL) and dried over magnesium sulfate. The organic layer is concentrated under vacuum and the residue is purified by column chromatography (silica gel, 10% ethyl acetate in hexanes) to provide 458 mg of compound B (60%). The complete synthesis is illustrated in FIG. 4.

후처리

  1. customthe organic layer quickly separated
  2. extractionThe organic layer is re-extracted with methylene chloride (2×20 mL)
  3. washthe combined organic layers were washed once with brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic layer is concentrated under vacuum
  6. customthe residue is purified by column chromatography (silica gel, 10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-4b856796121f4e63ac81eaa51146ff53
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173710B2

반응 노트

불러오는 중…