Dichloromethane → 5-Ethylnaphthalen-1-ol

HRID 1727275노트

반응식

HRID 1727275 반응식
ClCCl.C[O:5][C:6]1[C:15]2[C:10](=[C:11]([CH2:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.B(Br)(Br)Br>O>[CH2:16]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[CH:8][CH:7]=[C:6]2[OH:5])[CH3:17]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 123363811-Ethyl-5-methoxynaphthalene

생성물 1

HCID 123363835-Ethylnaphthalen-1-ol수율 75%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

Anhydrous dichloromethane (20 mL) was added to 8 (870 mg, 4.6 mmol). After cooling to 0° C., BBr3 (boron tribromide 1.0M in dichloromethane) (14 mL, 14 mmol) was added dropwise. The reaction mixture was heated to reflux for 5 h. After cooling, a large amount of water was slowly added and the mixture was extracted three times with dichloromethane. The organic layer was evaporated and the residue was purified on MPLC to afford compound 9c, 75% yield; MS-ESI− (m/z, %): 171 (M+−1, 100), 172 (M+, 45); 1H NMR δ 1.37 (3H, t, J=7.8 Hz, CH3CH2—), 3.10 (2H, q, J=7.8 Hz, CH3CH2—), 5.19 (1H, s, OH), 6.82 (1H, d, J=7.8 Hz, H-2), 7.31-7.45 (3H, m, H-3, 6, 7), 7.65 (1H, d, J=8.7 Hz, H-4), 8.06 (1H, d, J=8.1 Hz, H-8).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted three times with dichloromethane
  5. customThe organic layer was evaporated
  6. customthe residue was purified on MPLC

출처 및 근거

ORD 기록
ord-64a586c6ac184fb3ba227ce544f60d7f
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495026B2

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