Aluminium lithium hydride → 2-((tetrahydro-2H-pyran-2-yl)oxy)-cyclopentanemethanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)=O)C>O1CCCC1>[O:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[O:17][CH:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[CH2:10][OH:9]Participants
4
Conditions
- Temperature
- 25 °C
Procedure
A slurry of lithium aluminum hydride (883 mg, 23.27 mmol) in tetrahydrofuran (19.4 mL) cooled to 0° C. was treated with 2-(tetrahydro-pyran-2-yloxy)-cyclopentanecarboxylic acid ethyl ester (4.7 g, 19.59 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was poured onto ice/water. This mixture was filtered through a pad of celite (methylene chloride as eluent). The organics were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give [2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-methanol (3.25 g, 83.6%) as a clear liquid: EI-HRMS m/e calcd for C11H20O3 (M+) 200.1412 found 200.1412.
Workup
- additionAt this time, the reaction was poured onto ice/water
- filtrationThis mixture was filtered through a pad of celite (methylene chloride as eluent)
- washThe organics were washed with a saturated aqueous sodium chloride solution (1×100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ca9f5d17356f4c86b560b9f39585210b
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105671B2
Reaction notes
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