Hydrochloric Acid → ethyl 8-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-4H-spiro[naphthalene-1,4'-pyran]-3-carboxylate

HRID 1868940노트

반응식

HRID 1868940 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[C:8](/[OH:15])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]=1[C:16]1([C:22](OCC)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CC[O-].[Na+].Cl>CCO.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:16]1([CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:22](=[O:23])[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]2[OH:15]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 86629261(Z)-ethyl 4-(2-chloro-6-(3-ethoxy-1-hydroxy-3-oxoprop-1-enyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate

생성물 1

HCID 67099930ethyl 8-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-4H-spiro[naphthalene-1,4'-pyran]-3-carboxylate수율 80.5%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of (Z)-ethyl 4-(2-chloro-6-(3-ethoxy-1-hydroxy-3-oxoprop-1-enyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate (0.38 g, 0.99 mmol) in 5 mL EtOH was treated with NaOEt (freshly made from 0.1 g Na and 5 mL EtOH), and stirred at 60° C. for 2 hours. The mixture was cooled to room temperature and diluted with 100 mL EtOAc, neutralized with 5N HCl to pH 5, washed with water (20 mL), saturated NaCl (20 mL), dried over anhydrous sodium sulfate and concentrated. The concentrate was purified by column chromatography (10-40% EtOAc/hexane) to give 0.27 g yellow solid. MS m/e: (M+H)+ 337.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water (20 mL), saturated NaCl (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by column chromatography (10-40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-05d9249ad98a4b828a33d99ec5771dec
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635715B2

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