Tetrahydrofuran → 2-Hydroxymethyl-tetrahydro-pyranol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([CH:12]1[CH2:17][C:16](=O)[CH2:15][CH2:14][O:13]1)=O)C.C1C[O:22]CC1>>[OH:9][CH2:10][C:12]1([OH:22])[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.), stirred suspension of LiAlH4 (3.42 g, 90.0 mmol) in anhydrous THF (50 mL) was added dropwise a solution of 4-oxo-tetrahydro-pyran-2-carboxylic acid ethyl ester (5.17 g, 30.0 mmol). After stirring for 1 hour, the reaction was quenched by the slow, sequential addition of water (3.4 mL), 15% NaOH (3.4 mL), and water (10.0 mL). The inorganic salt was filtered off and extracted with EtOAc repeatedly since the product was absorbed on the solid. Solvent removal afforded 2.42 g (61%) of yellow oil. The crude mixture was carried to the next step without purification.
Workup
- stirringAfter stirring for 1 hour
- customthe reaction was quenched by the slow,
- additionsequential addition of water (3.4 mL), 15% NaOH (3.4 mL), and water (10.0 mL)
- filtrationThe inorganic salt was filtered off
- extractionextracted with EtOAc repeatedly since the product
- customwas absorbed on the solid
- customSolvent removal
Sources & evidence
- ORD record
- ord-45b7851e6e554fe494ac0c915fc2ef75
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06284764B1
Reaction notes
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