3,4-dihydro-2H-pyran → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 1514332Notes

Reaction equation

HRID 1514332 reaction equation
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[CH2:1]([O:5][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:23]1)[CH2:2][C:3]#[CH:4]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 693893-Buten-1-olHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-butyn-1-ol 1 (1.00 g, 14.3 mmol) and PPTS (0.72 g, 2.9 mmol) in CH2Cl2 (20 mL) was treated dropwise with dihydropyran (1.7 mL, 19 mmol) and the resulting mixture was stirred for overnight. The reaction mixture was diluted with CH2Cl2 (80 mL) and washed with 0.02 N NaOH (50 mL) and brine (100 mL). The organic layer was dried over MgSO4 and concentrated and the residue was purified with 3-5% EtOAc in hexane on silica gel to give 1.90 g of compound 2 (12.3 mmol, 86% yield): 1H NMR (CDCl3) δ 4.63 (t, J=3.4 Hz, 1H), 3.92˜3.77 (m, 2H), 3.59˜3.45 (m, 2H), 2.47 (td, J=7.1, 2.8 Hz, 2H), 1.96 (t, J=2.5 Hz, 1H), 1.90˜1.44 (m, 6H).

Workup

  1. washwashed with 0.02 N NaOH (50 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified with 3-5% EtOAc in hexane on silica gel

Sources & evidence

ORD record
ord-d97e165ccbf7459881ebec9a3a84d76c
Source dataset
uspto-grants-2012_07
Patent number
US08222257B2

Reaction notes

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