3,4-dihydro-2H-pyran → 6-Chloro-2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

HRID 1798052노트

반응식

HRID 1798052 반응식
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[CH:5]=[C:4]([OH:11])[CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[CH:5]=[C:4]([O:11][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:3]=1

참가 물질

4

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 232948482-Chloro-4,6-dihydroxybenzaldehyde

생성물 1

HCID 866539726-Chloro-2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde수율 87.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-chloro-2,4-dihydroxybenzaldehyde (9.0 g, 52.2 mmol) in DCM (150 mL) was added 3,4-dihydro-2H-pyran (9 mL, 98.4 mmol), followed by PPTs (1.31 g, 5.2 mmol). The reaction mixture was stirred at room temperature for 1.5 h and quenched by saturated aqueous NaHCO3 (50 mL) at 0° C. The organic layer was separated, washed with brine (40 mL) and dried over anhydrous Na2SO4. Concentration in vacuo followed by purification with column chromatography on silica gel (EtOAc/PE=1:100) gave the title compound as a colorless oil (10.5 g, Yield: 87.3%). 1H NMR (400 MHz, DMSO-d6) δ12.00 (s, 1H), 10.17 (s, 1H), 6.72-6.78 (m, 1H), 6.57-6.64 (m, 1H), 5.50-5.70 (t, 1H), 3.60-3.73 (m, 2H), 1.55-1.87 (m, 6H) MS (ESI) m/z=257 [M+H]+.

후처리

  1. customquenched by saturated aqueous NaHCO3 (50 mL) at 0° C
  2. customThe organic layer was separated
  3. washwashed with brine (40 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationConcentration in vacuo
  6. customfollowed by purification with column chromatography on silica gel (EtOAc/PE=1:100)

출처 및 근거

ORD 기록
ord-b798f3974ad94b8fae994283a4c10173
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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