Diethyl Ether → Tetrahydropyranyl ether

HRID 1490134Notes

Reaction equation

HRID 1490134 reaction equation
[Si](O[C@H:9]1[CH2:13][C@@H:12]([OH:14])[CH:11]=[CH:10]1)(C(C)(C)C)(C)C.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.CC[O:23]CC>C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[O:23][CH:12]1[CH2:13][CH2:9][CH2:10][CH2:11][O:14]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 80803,4-dihydro-2H-pyranHCID 10910904(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol

Product 1

HCID 263182Tetrahydropyranyl ether

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of (1R,4S)-4-(tert-butyldimethylsilyl)oxy-2-cyclopentenol (9.70 g, 40 mmol) (J. Amer. Chem. Soc., 1991, 113, 9851,), dihydropyran (4.40 g, 53.0 mmol) and p-toluenesulfonic acid (100 mg) in dry ether (50 ml) was stirred for 10 h at room temperature. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (50 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford 14.2 g of crude tetrahydropyranyl ether of (1R,4S)-4-(tert-butyldimethylsilyl)oxy-2-cyclopentenol as a colorless oil.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (50 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d9c25bec53c2446f8c22f11be3de5bd6
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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