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

HRID 1798052ノート

反応式

HRID 1798052 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-b798f3974ad94b8fae994283a4c10173
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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