3,4-dihydro-2H-pyran → 3-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehyde

HRID 1755780Notes

Reaction equation

HRID 1755780 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C([O-])(=O)C.[NH4+]>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 517165Ammonium AcetateHCID 131314553-(Hydroxymethyl)benzaldehyde

Product 1

HCID 190029373-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the alcohol of Step 1 (94 g) in CH2Cl2 (1.5 L) at 0° C. was added 3,4-dihydro-2H-pyran (300 mL) followed by pyridinium p-toluenesulfonate (5.0 g). After 3 hours at room temperature, the reaction mixture was poured on aqueous 25% ammonium acetate and extracted with CH2Cl2. The resulting mixture was purified by flash chromatography (50% EtOAc in toluene) to give 147 g of the title aldehyde.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe resulting mixture was purified by flash chromatography (50% EtOAc in toluene)

Sources & evidence

ORD record
ord-24725498daac4dffa10b22db9532a20b
Source dataset
uspto-grants-1995_08
Patent number
US05438141

Reaction notes

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