Ethyl oxoacetate → 7-Bromo-3-methylnaphthalen-1-ol

HRID 926149

반응식

HRID 926149 반응식
ClC1C=C2C(=CC=1)C(O)=CC(C)=C2.BrC1C=CC(CC(=O)C)=CC=1.[Br:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[C:31]([CH3:37])[CH:32]=[C:33]2[OH:36])=[CH:28][CH:27]=1.[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH:39]=[O:40]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[C:31]([CH3:37])[CH:32]=[C:33]2[OH:36])=[CH:28][CH:27]=1.[Br:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[C:31]([CH3:37])[C:32]([CH:39]([OH:40])[C:38]([O:42][CH2:43][CH3:44])=[O:41])=[C:33]2[OH:36])=[CH:28][CH:27]=1

참가 물질

8

반응물 4

HCID 70211Ethyl oxoacetateHCID 7363321-(4-Bromophenyl)propan-2-oneHCID 671262827-Bromo-3-methylnaphthalen-1-olHCID 896768476-Chloro-3-methylnaphthalen-1-ol

생성물 2

HCID 671262827-Bromo-3-methylnaphthalen-1-olHCID 89676857Ethyl 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

7-Bromo-3-methylnaphthalen-1-ol was prepared in a similar manner as 6-chloro-3-methylnaphthalen-1-ol in Example 5 except using 1-(4-bromophenyl)propan-2-one instead of 1-(3-chlorophenyl)propan-2-one. To a solution of 7-bromo-3-methylnaphthalen-1-ol (11.5 g, 48.5 mmol) in dichloromethane (145 mL) at 0° C. was added a 1 M titanium(IV) chloride solution in dichloromethane (48.5 mL, 48.5 mmol) and stirred for 20 min. Ethyl glyoxylate (50% solution in PhCH3, 10.6 mL, 53.3 mmol) was added over 15 minutes and stirred for 1 hour at 0° C. The reaction was quenched by the addition of Rochelle's salt solution and stirred at room temperature for 14 hours. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried, filtered, concentrated and purified by flash column chromatography (EtOAc/Hexanes) to provide the desired product. 1H-NMR: 400 MHz, (CDCl3) δ: 8.52 (s, 1H), 8.34 (s, 1H), 7.49 (m, 2H), 7.13 (s, 1H), 5.67 (s, 1H), 4.24 (m, 1H), 4.16 (m, 1H), 2.29 (s, 3H), 1.23 (m, 3H).

후처리

  1. stirringstirred for 1 hour at 0° C
  2. customThe reaction was quenched by the addition of Rochelle's salt solution
  3. stirringstirred at room temperature for 14 hours
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash column chromatography (EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-58dc057988764d43a99bee0658efa575
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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