2-Methylbenzenesulfonic acid → HCID 10731287, compound

HRID 1417577Notes

Reaction equation

HRID 1417577 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].C1(C)C(S(O)(=O)=O)=CC=CC=1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1>C(Cl)Cl>[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8200Tetraethylene Glycol

Product 1

HCID 10731287HCID 10731287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL solution of methylene chloride containing tetraethylene glycol (15 mmol, 2.91 g) and toluenesulfonic acid (20 mg) was added dropwise via syringe 3,4-dihydro-2H-pyran (12 mmol, 1.0 g, 1.1 mL). The reaction mixture was stirred for 3.5 h, and the solvent was removed by rotary evaporation. Mono-tetrahydropyran 1 was isolated by flash chromatography on silica eluting with 1:1 tetrahydrofuran/methylene chloride, affording 1.82 g of a clear, colorless oil (44% yield). 1H NMR (400 MHz, CDCl3): δ4.61 (dd, 1H, J1 =J2 =4 Hz), 4.6-4.8 (m, 2H), 3.69 (t, 2H, J=7 Hz).

Workup

  1. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-df13dcd0665544a484e5254cf01ca0bd
Source dataset
uspto-grants-1999_03
Patent number
US05877214

Reaction notes

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