Dichloromethane → 5-Ethylnaphthalen-1-ol

HRID 1713715ノート

反応式

HRID 1713715 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 123363835-Ethylnaphthalen-1-ol収率 75%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-94a68af97b2248f1bfeacbbdf6bf9b6c
出典データセット
uspto-grants-2010_09
特許番号
US07795299B2

反応ノート

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