benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate → 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropanol

HRID 2068186Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]([O:12]CC1C=CC=CC=1)=O.[CH3:20][CH2:21][Mg+].[Br-]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([OH:12])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 18 °C

Procedure

To a mixture of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate (150 mg, 0.568 mmol) in 2 mL of THF was added Ti(Oi-Pr)4 (0.18 mL, 0.568 mmol, d=0.955 g/L, Ardrich) via a syringe under nitrogen at rt. After stirring at 18° C. for 30 min, EtMgBr (0.48 mL, 1.42 mmol, 3M ether solution, Aldrich) was added via a syringe pump over 2 hrs. The reaction was quenched with 5 mL of water, after benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate was consumed completely (monitored by TLC). The mixture was filtered through a celite pad and the filtrate was extracted with ethyl acetate (30 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (10:1 (v/v) petroleum ether/EtOAc) to afford 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropanol as colorless oil (60 mg, 57%).

Workup

customThe reaction was quenched with 5 mL of water
customafter benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate was consumed completely (monitored by TLC)
filtrationThe mixture was filtered through a celite pad
extractionthe filtrate was extracted with ethyl acetate (30 mL×3)
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (10:1 (v/v) petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-16782d59cb79444791650d85cf482329
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293897B2

Reaction notes

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