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

HRID 1798052Notes

Reaction equation

HRID 1798052 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-b798f3974ad94b8fae994283a4c10173
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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