Triethylamine → 7-[(tertButyldimethylsilyl)oxy]-6-methoxy-1-tetralone

HRID 1357875

반응식

HRID 1357875 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].CCN(CC)CC.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:23]([Si:26]([CH3:28])([CH3:27])[O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14])([CH3:25])([CH3:24])[CH3:22]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 3168407-Hydroxy-6-methoxy-1-tetralone

생성물 1

HCID 222447927-[(tertButyldimethylsilyl)oxy]-6-methoxy-1-tetralone수율 95.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a well-stirred solution of 7-Hydroxy-6-methoxy-1-tetralone (80.0 mg, 0.42 mmol) in CH2Cl2, was added Et3N (47 mg, 0.46 mmol), followed by DMAP (5.1 mg, 0.042 mmol) and TBSCl (69 mg, 0.46 mmol) at 0° C. under dry nitogen. After 2 h (at rt), the mixture was partitioned between CH2Cl2 and water. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 7-[(tertButyldimethylsilyl)oxy]-6-methoxy-1-tetralone (122 mg, 0.40 mmol, 95%) was obtained following purification by column chromatography. 1H-NMR (CDCl3, 300 MHz) 0.15 (s, 6H), 0.99 (s, 9H),2.11 (m, 2H), 2.58 (t, J=6.1 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 3.86 (s, 3H), 6.63 (s, 1H), 7.56 (s, 1H).

후처리

  1. customunder dry nitogen
  2. customthe mixture was partitioned between CH2Cl2 and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationafter filtration
  5. concentrationthe organic layer was concentrated in vacuo
  6. customto provide a yellow oil

출처 및 근거

ORD 기록
ord-25ae7239fa944431863590942a22692e
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593374B2

연결된 노트

불러오는 중…