Tetrahydro-4H-pyran-4-one → HCID 10559661, compound

HRID 1737293Notes

Reaction equation

HRID 1737293 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH2:8]([Mg]Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([C:4]1([OH:7])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418336HCID 178418336, compound

Product 1

HCID 10559661HCID 10559661, compoundYield 87.5%

Procedure

Tetrahydropyran-4-one (4.34 g, 43.4 mmol) is treated with benzylmagnesium chloride (2 M in THF, 32.5 mL, 65.0 mmol) according to general procedure A. The crude product is filtered through silica gel, first with CH2Cl2, then with 1:1 hexane/EtOAc, to give alcohol 17 as a colorless oil (7.3 g, 87%) . 1H NMR (CDCl3) 7.40-7.15(m,5), 3.80-3.65(m,4), 2.77(s,2), 1.81(s,1), 1.80-1.70(m,2), 1.50-1.40(m,2); 3C NMR(CDCl3) 135.90, 130.53, 128.32, 126.74, 68.55, 63.65, 49.42, 37.46; MS(MW=192.3, CI/CH4, eE=70eV) m/z 193 (M+H)+, 191, 176, 175(base peak), 157, 145, 129, 119, 101, 92, 83, 71.

Workup

  1. filtrationThe crude product is filtered through silica gel, first with CH2Cl2

Sources & evidence

ORD record
ord-baa7b10a6eef4af2ad1141b5fbaf53a3
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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