Aluminium lithium hydride → [1-(Tetrahydro-pyran-2-yloxy)-cyclopropyl]-methanol

HRID 546120Notes

Reaction equation

C[O:2][C:3]([C:5]1([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[O:8][C:5]1([CH2:3][OH:2])[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 25 °C

Procedure

1-(Tetrahydro-pyran-2-yloxy)-cyclopropanecarboxylic acid methyl ester (3.50 g, 17.50 mmol) was dissolved in diethyl ether (85 mL) and a 2.0 M solution of lithium aluminum hydride in diethyl ether (8.75 mL, 17.50 mmol) was added. Upon complete addition, the reaction was refluxed under nitrogen for 1 h. Upon cooling to 25° C., the excess lithium aluminum hydride was hydrolyzed by the addition of ice chips. The organic layer was seated, washed with water (2×20 mL), dried over magnesium sulfate and concentrated in vacuo to afford [1-(tetrahydro-pyran-2-yloxy)-cyclopropyl]-methanol (2.81 g, 93%) as a clear, thick oil: H1-NMR (400 MHz, CDCl3) δ 0.5-1.0 (4H, m), 1.40-2.0 (6H, m), 3.0-3.2 (2H, m), 3.3-4.3 (2H, m), 4.5-4.7 (1H, m), 4.75-5.0 (1H, m).

Workup

additionUpon complete addition
temperaturethe reaction was refluxed under nitrogen for 1 h
washwashed with water (2×20 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-08b51af0a0164487830068395019fa34
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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